Category: alcohols-buliding-blocks

Electric Literature of 2867-59-6 ,Some common heterocyclic compound, 2867-59-6, molecular formula is C4H11NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2-(3-Fluorophenyl)-3-oxo-6-[4-(trifluorom acid (100 mg, 0.26 mmol) was dissolved in anhydrous DMF (2.0 ml_). (3RS)-3-Aminobutan-1 -ol (47.1 mg, 0.53 mmol), N-ethyl-N-isopropylpropan-2-amine (0.207 ml_, 1.19 mmol), and propane phosphonic acid anhydride (T3P, 231 muIota_, 50% in DMF, 397 muetaiotaomicronIota) were successively added. It was stirred at rt overnight. The crude reaction mixture was purified by RP-HPLC (column: X-Bridge C18 5muetaiota 100x30mm, mobile phase: (water + 0.1 vol% formic acid (99%)) / acetonitrile, gradient) to yield 88.3 mg (74%) of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm] = 1 .19 (d, 3H), 1.60 – 1.74 (m, 2H), 3.45 – 3.51 (m, 2H), 4.09 – 4.21 (m, 1 H), 4.51 (t, 1 H), 7.36 – 7.43 (m, 1 H), 7.54 – 7.58 (m, 1 H), 7.59 – 7.66 (m, 2H), 7.88 (d, 2H), 8.20 (d, 2H), 8.70 (s, 1 H), 9.29 (d, 1 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 2867-59-6, 3-Aminobutan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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Synthetic Route of 26021-57-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 26021-57-8, name is 3,4-Dihydro-2H-benzo[b][1,4]oxazin-6-ol. This compound has unique chemical properties. The synthetic route is as follows.

a) (S)-3-(3,4-Dihydro-2H-benzo[1,4]oxazin-6-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester A solution of 3,4-dihydro-2H-benzo[1,4]oxazin-6-ol (CAS registry 26021-57-8) (4.0 g, 26.5 mmol) in DMF (150 ml) was treated with NaH (2.117 g, 52.9 mmol) for 20 min at 20 C. (R)-3-Methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (CAS registry 127423-61-4) (9.13 g, 34.4 mmol) was added. After stirring for 22 h at rt the reaction mixture was concentrated to dryness, then taken up with EtOAc, filtered through hyflo and the filtrate was washed with sat. aq. Na2CO3 solution. Combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (cyclohexane/isopropanol 100:0 to 85:15 in 40 min) to provide the title compound as a yellow oil. HPLC RtM8=1.84 min; ESIMS: 321 [(M+H)+]. 1H NMR (400 MHz, DMSO): 6.52 (d, 1H), 6.12 (d, 1H), 6.02 (m, 1H), 5.76 (m, 1H), 4.75 (br s, 1H), 4.01-40.5 (m, 2H), 3.27-3.50 (m, 4H), 3.22-3.26 (m, 2H), 1.95-2.08 (m, 2H), 1.39 (m, 9H).

According to the analysis of related databases, 26021-57-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
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Electric Literature of 75853-18-8 , The common heterocyclic compound, 75853-18-8, name is 2,3-Difluorobenzyl alcohol, molecular formula is C7H6F2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 73 2,3-Difluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate hydrochloride was prepared from cis 1-chlorocarbonyl-2,6-dimethyl-4-tert-butoxycarbonylpiperazine and 2,3-difluorobenzyl alcohol according to the methods described for Examples 52 and 54 to give the product as a white solid (0.1846 g, 57percent overall); (Found: C, 52.4; H, 6.0; N, 8.6percent. C14H18F2N2O2.HCl requires C, 52.4; H, 6.0; N, 8.7percent); deltaH (400 MHz, DMSO-d6) 10.07 (1H, br), 9.33 (1H, br), 7.44 (1H, m), 7.28 (2H, m), 5.21 (2H, s), 4.30 (2H, m), 3.14 (2H, d, J 13.2 Hz), 3.06 (2H, m), and 1.31(6 H, d, J 7.2 Hz).

The synthetic route of 75853-18-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, David Reginald; Bentley, Jonathan Mark; Davidson, James Edward Paul; Dawson, Claire Elizabeth; George, Ashley Roger; Mansell, Howard Langham; Mattei, Patrizio; Mizrahi, Jacques; Nettekoven, Matthias Heinrich; Pratt, Robert Mark; Roever, Stephan; Roffey, Jonathan Richard Anthony; Specklin, Jean-Luc; Stalder, Henri; Wilkinson, Kerry; US2002/143020; (2002); A1;,
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Reference of 124937-73-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 124937-73-1, name is 3-(2-Methoxy-5-methylphenyl)-3-phenylpropan-1-ol, molecular formula is C17H20O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 1: Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl methane sulfonate (Vb)This intermediate is of significant importance for use in the preparation of Tolterodine or salts thereof, or its derivatives according to the present invention.In a 3-necked round bottom flask, 6-methyl-4-phenyl-3,4-dihydro coumarin (II, 10Og, 0.420 mol) is charged into methanol (500 ml) at about 250C with stirring. To the resulting suspension, potassium carbonate (K2CO3, 87 g, 0.63 mol) and methyl iodide (MeI, 78 ml, 1.25 mol) are added and the mass is stirred at from about 550C to about 6O0C for 4 h. The reaction mass is cooled to from about 400C to about 450C and MeI (27 ml, 0.43 mol) and K2CO3 (29 g, 0.21 mol) are added. Re-heat the mass to 55~ 6O0C and stir for additional 6 h until the reaction completes. Then solvent is removed by distillation under vacuum. The residue is dissolved in 350 ml of toluene. This organic phase is washed once with 750 ml of DM water and twice with 450 ml of DM water.The organic layer thus obtained is charged into a 3-necked round bottom flask under N2 atmosphere and cooled at temperature from about -50C to about 5C. Toluene solution of sodium bis(2-methoxyethoxy) aluminum hydride (Red-Al, 200 ml, 70% w/v, 0.706 mol) is slowly added through a dropping funnel over a period of 120 min, maintaining the solution temperature within -5 ~ 50C. The mixture is stirred for an additional 1 h at this temperature until the reaction completes. Then aqueous solution of NaOH (80 ml, 10%) is added through a dropping funnel over a period of 45 min, maintaining the temperature at 0 ~ 100C, and continue stirring for an additional 45 min at the same temperature. Add 750 ml of DM water and stir for 30 min at 250C. The biphasic reaction mass is filtered through a celite bed (10 g). The organic layer is collected and dried over 20 g of anhydrous sodium sulfate (Na2SO4). The solids are filtered and washed with 50 ml of toluene. The toluene is distilled off completely and compound IV is obtained as slightly yellow thick oil.The thick oil is dissolved in 300 ml of dichloromethane (DCM) under N2 atmosphere. Triethylamine (Et3N, 90 ml, 0.647 mol) is added and the mass is cooled to 0 ~ 5C. Mesyl chloride (MsCl, 36 ml, 0.465 mol) is added slowly through a dropping funnel over a period of 120 min, keeping the solution temperature below 1O0C. Continue stirring the mixture for an additional 1 h at 0~5C until the reaction completes. 1 L of cold DM water (0~5C) was added and the mass is stirred for 30 ~ 60 min at this temperature. Cone. HCl (25 ml) is added and the mass is stirred until it reaches 25C. The organic layer is collected and washed with 200 ml of DM water. About 180 ~ 220 ml of DCM is distilled off from the organic layer under atmosphere pressure at 38 ~ 43C. 400 ml of cyclohexane is added to the residue and the mass is heated to reflux till a clear solution is obtained (70 ~ 800C). This solution is cooled slowly and compound Vb crystallized. The solid is filtered in Buchner funnel and spray washed with 100 ml of cold cyclohexane. The mass is dried under vacuum at 600C to give 90 ~ 110 g of title compound.

According to the analysis of related databases, 124937-73-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMATHEN S.A.; KOFTIS, Theoharis, V.; NEOKOSMIDIS, Efstratios; SONI, Rohit, Ravikant; MANDALOU, Panagiota; MENISIOU, Aristotelis; WO2010/94292; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7735-42-4, 1,16-Hexadecanediol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 7735-42-4, blongs to alcohols-buliding-blocks compound. Recommanded Product: 7735-42-4

Synthesis Example C-(18) 1,16-Hexadecanediol (13.75 g) was dissolved in 37 ml of cyclohexane, and 57% hydrobromic acid solution (37 ml) was added to this solution. The reaction mixture was refluxed for six hours while stirring. After the reaction, the mixture was extracted three times with diethyl ether. The organic layer was neutralized with saturated sodium hydrogen carbonate solution, washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane: ethyl acetate = 7:3) gave 16-bromohexadecan-1-ol as white crystals at a 67% yield. Molecular weight: 320.9 (C16H33BrO) TLC: (hexane-ethyl acetate 7-3) Rf value=0.53 1H-NMR: (300MHz, CDCl3)delta: 1.26 (s large, 24H, -(CH2)12-); 1.56 (qt, 2H, J=7.2Hz, -CH2-); 1.85 (qt, 2H, J=7.1 Hz, -CH2-); 3.40 (t, 2H, J=7.1Hz, -CH2-Br); 3.63 (t, 2H, J=6.6Hz, -CH2-O-) 13C-NMR: (75MHz, CDCl3) delta: 25.84; 27.28; 28.22; 29.48-29.50; 32.90; 33.20; 34.01; 63.01

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7735-42-4, 1,16-Hexadecanediol, and friends who are interested can also refer to it.

Reference:
Patent; Meiji Dairies Corporation; EP1854777; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13726-17-5, (4-Chloro-3-methoxyphenyl)methanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C8H9ClO2, blongs to alcohols-buliding-blocks compound. Computed Properties of C8H9ClO2

D. Synthesis of 4-chloro-3-methoxybenzaldehyde (0202) To a solution of (4-chloro-3-methoxyphenyl)methan-1-ol (5.08 g, 29.4 mmol) in benzene (120 mL) was added MnO2 (5.65 g, 65 mmol). The reaction mixture was refluxed for 17 hr, chilled, and filtered through Celite, washing the cake with CH2Cl2 (300mL). The filtrate was concentrated in vacuo to give 4-chloro-3-methoxybenzaldehyde (4.5 g, 89%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13726-17-5, (4-Chloro-3-methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Portola Pharmaceuticals, Inc.; Scarborough, Robert; Jantzen, Hans-Michael; Huang, Wolin; Sedlock, David; Marlowe, Charles; Kane-Maguire, Kim; (200 pag.)EP2314593; (2016); B1;,
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Related Products of 162358-05-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 162358-05-6, name is 2-(4-Octylphenyl)ethanol. A new synthetic method of this compound is introduced below.

Example 6 Preparation of Compound of Formula VIIIn a round bottom flask, 600 ml of methylene chloride was charged and 100 gm of compound of Formula V, obtained as in Example 4, and 5.0 gm of DMAP and 110 gm of triethyl amine was added. The reaction mass was stirred for about 10 minutes and cooled at about 0-5 C. 75 gm of methane sulphonyl chloride was added at about 0-5 C. and the temperature of reaction mass was raised to about 25-30 C. The reaction mass was stirred at about 25-30 C. for about 1 hour and water (500 ml) was added to the reaction mass. The pH was adjusted to about 2-4 by using aq. HCl and the reaction mass was stirred for about 20 min. The organic layer was separated and washed with 7% bicarbonate solution followed by washing with brine. The organic layer was treated with charcoal and distilled out under vacuum and degassed to get 110 gm of compound of Formula VI.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,162358-05-6, 2-(4-Octylphenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Glenmark Generics Limited; Gharpure, Milind; Narawade, Krishna; Chand, Prem; Bhirud, Shekhar; US2015/18578; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4728-12-5, (2,2-Dimethyl-1,3-dioxan-5-yl)methanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, HPLC of Formula: C7H14O3, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C7H14O3

A solution of (2,2-dimethyl-1 ,3-dioxan-5-yl)methanol (2.51 g, 17.1 mmol) and N, N- dimethylaminopyiridine (208 mg, 1.7 mmol) in dichloromethane (100 ml.) was cooled to 0 0C and p-toluenesulfonyl chloride (3.59 g, 18.8 mmol) and triethylamine (4.8 ml. 34.2 mmol) were added. The mixture was stirred overnight at rt, diluted with water, and the organic layer was separated. The solvent was removed and the crude material was purified via silica gel chromatography to give 4.16 g of the title compound. 1H NMR (DMSOd6) delta 7.78 (d, 2 H), 7.47 (d, 2 H), 4.09 (d, 2 H), 3.84 (dd, 2 H), 3.52 (dd, 2 H), 2.41 (s, 3 H), 1.79 – 1.94 (m, 1 H), 1.28 (s, 3 H), 1.18 (s, 3 H).

The synthetic route of 4728-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157330; (2008); A1;,
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Application of 626-18-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 626-18-6, name is 1,3-Benzenedimethanol. This compound has unique chemical properties. The synthetic route is as follows.

1,3-phenylenedimethanol (2.18 g, 15.778 mmol) was dissolved in DMF (21.80 ml) and cooled to 0 C, Imidazole (2.148 g, 31.557 mmol) was added followed by the addition of tert-Butyldimethylchlorosilane (2.378 g, 15.778 mmol). The mixture was stirred at 0 C for 1 h and allowed to warm up to r.t. and stirred overnight. Upon completion of the reaction, the mixture was quenched with sat. aq. NH4C1 (10 ml), extracted with EtOAc (2 x 100 ml). The organic layer was washed with sat. aq. NaHC03solution (10 ml), dried over Na2S04and concentrated. The residue was purified by flash chromatography to give (3-(((tert-butyldimethylsilyl)oxy)methyl)phenyl)methanol (393) as colorless oil (1.73 g, 43.4% yield)

According to the analysis of related databases, 626-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MAN CO LTD; E Ja I Al Aendeu D Maenijimeonteu Gabu Siki Ga I Sya; ZHENG WANJUN; Jaeng , -wan-jun; ZHU XIAOJIE; Ju , -sya-o-ji-e; DU HONG; Du , -hong; POSTEMA MAARTEN; Po Seu-te-ma-, -ma-a-reu-ten; JIANG YIMIN; Jang , -w-min; LI JING; Ri , -jing; YU ROBERT; Yu , -ro-beo-teu; CHOI HYEONG WOOK; Choe , -hyeong—uk; LEE JAEMOON; I , -jae-mun; FANG FRANK; Paeng , -peu-rang-keu; CUSTAR DANIEL; Ku Seu-ta-, -da-ni-el; (178 pag.)KR2018/83863; (2018); A;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 597-31-9, 3-Hydroxy-2,2-dimethylpropanal, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Recommanded Product: 3-Hydroxy-2,2-dimethylpropanal, blongs to alcohols-buliding-blocks compound. Recommanded Product: 3-Hydroxy-2,2-dimethylpropanal

EXAMPLE 1Preparation of an Aqueous Polymethylol Mixture by the Hydrogenation ProcessStage a) Aldol Reaction:Approx. 750 g/h of isobutyraldehyde (approx. >99.5 GC area % of IBA) were reacted with approx. 700 g/h of formaldehyde (approx. 49% formaldehyde, 1.5% of methanol, remainder water) and 80 g/h of trimethylamine solution (50% TMA in water) in a two-stage stirred tank cascade.Stage b) Distillative Separation of the Reaction Mixture from Stage a):Subsequently, the solution was freed of low boilers by distillation in a column. The column was equipped with 1.5 m of fabric packing (specific surface area 500 m2/m3) in the rectifying section and 4 m of sheet metal packing (250 m2/m3). The aldolization discharge was fed in above the sheet metal packing. At the top of the column, a condenser with cooling water (approx. 10 C.) and a downstream phase separator was used. At the top, the distillate was fed to the condenser in gaseous form. Approx. 255 g/h of liquid condensate were obtained. In the phase separator connected downstream, an aqueous phase of 95 g/h was removed and fed completely to the column. In addition, 135 g/h were fed from the phase separator to the first stirred tank. In order to maintain the regulation temperature in the column at 85 C., 25 g/h of organic phase were additionally fed to the column. In the cold trap connected downstream of the condenser, approx. 1 g/h of liquid was obtained (approx. 80% IBA, approx. 20% TMA), which was likewise recycled.The IBA removal was conducted at a top pressure of approx. 1 bar absolute. The evaporator used was a falling film evaporator. A bottom temperature in the bottom of the column of 104 C. was established. The reflux rate (i.e. cooling water rate of the partial condenser) to the column was regulated by means of the temperature in the middle of the fabric packing; a temperature of 85 C. was established.By means of a pump, approx. 100 kg/h of liquid were drawn off from the bottom of the column. This was fed to the falling film evaporator (consisting of an oil-heated stainless steel tube, length 2.5 m, internal diameter approx. 21 mm, wall thickness approx. 2 mm). Approx. 1.5 kg/h of product with a concentration of approx. 0.3% isobutyraldehyde were drawn off from the bottom of the falling film evaporator. The vapors and excess liquid were fed to the bottom of the column. The bottom product discharged comprised approx. 70% by weight of HPA, approx. 1.5% by weight of HPN, 0.3% by weight of IBA, remainder water.Stage c) Hydrogenation of the Bottom Discharge from Stage b):The resulting bottom product was subsequently subjected to a hydrogenation by means of a fixed bed.The catalyst was activated as follows:150 ml of a Cu/Al2O3 catalyst as described in EP 44444 and PF57216 were activated in a tubular reactor at 190 C. by passing over a mixture of 5% by volume of hydrogen and 95% by volume of nitrogen (total volume 50 l (STP)/h) at ambient pressure for 24 hours.The hydrogenation was performed as follows:The starting solution used was the mixture described above as hydrogenation feed. Approx. 10% by weight based on the hydrogenation feed of a 15% aqueous solution of trimethylamine was added to the mixture. The feed thus obtained was conducted in trickle mode at H2 pressure 40 bar through the reactor heated to 120 C. The space velocity was 0.4 kg of HPA/(Icat*h). A portion of the hydrogenation discharge was added again to the feed (circulation mode). The ratio of circulation to feed was 10:1. The pH of samples of the reactor discharge at room temperature was measured at 8.9.The composition of the aqueous polymethylol mixture from stage c) was:NPG: 69% by weight Methanol: 3.5% by weight TMA: 2% by weight. organic secondary compounds (HPA, isobutanol): <2% by weight TMA formate: 1% by weight Water: 23% by weight At the same time, in my other blogs, there are other synthetic methods of this type of compound,597-31-9, 3-Hydroxy-2,2-dimethylpropanal, and friends who are interested can also refer to it. Reference:
Patent; BASF-SE; US2012/4472; (2012); A1;,
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