Category: alcohols-buliding-blocks

Synthetic Route of 150192-39-5, 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 150192-39-5, name is (2-Bromo-5-methoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Preparative Example 91 Preparation of 5-methoxy-1,3-dihydro-1-hydroxy-2,1-benzoxaborole 2-bromo-5-methoxybenzylalcohol (6.5 parts; 0.03M) was dissolved in dry THF (100 ml) and cooled to -78 C. n-Butyl-lithium (26.4 ml of a 2.5M solution in hexanes ex Aldrich, 0.066M) was added over 20 minutes with stirring under a nitrogen blanket and keeping the temperature below -60 C. After stirring for a further hour at -70 C. HPLC showed the reaction to be incomplete with 20% starting material remaining. A further aliquot of n-butyl-lithium in hexanes (5 ml; 0.0125M) was added and the reactants allowed to warm to -50 C. Tributylborate (17.8 ml; 0.066M) was then added at between -70 and -50 C. with stirring under a nitrogen blanket and the reactants allowed to warm to about 20 C. Water (20 ml) was added and the pH adjusted to 10 with hydrochloric acid. After washing with diethylether, the pH of the aqueous phase was adjusted to pH 1-2 with hydrochloric acid and washed with diethyl ether. The ether extract was washed with aqueous saturated brine, dried over anhydrous magnesium sulphate and the ether evaporated to leave the product as a pale oil (3.7 parts). This was slurried with water containing a little methanol whereupon a pinkish-white solid separated which was filtered, washed with water and dried (2.0 parts) mp=110-115 C. after recrystallisation from aqueous methanol.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 150192-39-5, (2-Bromo-5-methoxyphenyl)methanol.

Reference:
Patent; Zeneca Limited; US5880188; (1999); A;,
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Synthetic Route of 10602-04-7 ,Some common heterocyclic compound, 10602-04-7, molecular formula is C9H8O, 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.

To a solution of (4-ethynylphenyl)methanol (1.66 g, 12.54 mmol) and imidazole (1.71 g, 25.08 mmol) in DMF (37mL) was added TBDMSCl (2.84 g, 18.81 mmol). This reaction mixture was stirred at ambient temperature for overnight. All the volatile solvent was removed under reduced pressure, and the residue was dissolved in DCM (10 ml). Water (10 mL) was added, and the aqueous layer was extracted with DCM (10 mL X 2). The combined organic layer was washed with brine (20 mL), dried over Na2SO4, and filtered. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography, by column chromatography with hexane/ethyl acetate (10/1, v/v) to obtain the compound 59 as a brown solid (2.91 mg, 94percent yield): 1H NMR (400 MHz, CDCl3) _ 7.46 (d, J = 8.2 Hz, 2H), 7.28 (d, J = 8.8 Hz, 2H), 4.73 (s, 2H), 3.04 (s, 1H), 0.94 (s, 9H), 0.10 (s, 6H); 13C NMR (100 MHz, CDCl3) _ 142.5, 132.2, 126.0, 120.6, 83.9, 64.7, 26.1, 18.5, -5.1.

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. 10602-04-7, (4-Ethynylphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; DALBY, Kevin N.; EDUPUGANTI, Ramakrishna; TALIAFERRO, Juliana; LEE, Juhyeon; (0 pag.)WO2018/160967; (2018); A1;,
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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. 29055-08-1, name is (2-(Methylamino)phenyl)methanol, molecular formula is C8H11NO, 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. Product Details of 29055-08-1

General procedure: To a solution of 13 (500 mg, 1.86 mmol) in DMF (5.0 mL) were added N-methylaniline (241 muL, 2.23 mmol), 1-hydroxybenzotriazole (251 mg, 1.86 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (534 mg, 2.79 mmol) at room temperature. The reaction mixture was stirred at room temperature for 12 h. Water was then added, and the mixture was extracted with a mixture of toluene and EtOAc (1:1). The organic layer was washed with H2O and brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by silica gel column chromatography using hexane/EtOAc (1:1, v/v) as eluent. The solvent was removed in vacuo, and the resulting solid was recrystallized from iPrOH to give 14 (547 mg, 82percent) as a white solid

With the rapid development of chemical substances, we look forward to future research findings about 29055-08-1.

Reference:
Article; Fukaya, Takayuki; Kodo, Toru; Ishiyama, Takeo; Kakuyama, Hiroyoshi; Nishikawa, Hiroyuki; Baba, Satoko; Masumoto, Shuji; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5568 – 5582;,
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Synthetic Route of 40571-86-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.40571-86-6, name is Trans-2-(benzylamino)cyclohexanol, molecular formula is C13H19NO, molecular weight is 205.2961, as common compound, the synthetic route is as follows.

General procedure: In a typical reaction, 90mL dry acetonitrile solution of tetrabutylammonium tetrafluoroborate(0.1 M) as the supporting electrolyte in an undivided cell fitted with a sacrificial magnesium rod as an anode and a stainless steel grid (20 cm2) as the cathode was subjected to electrolysis at a constant current density (I = 80 mA/cm?2). The cell was cooled to ?20°C by immersing in the Lauder refrigerating system. During the electrolysis, the system was maintained under an inert atmosphere by continuous bubbling of nitrogen. The electrolysis was stopped after the formationof two equivalents of cyanomethyl anion with respect to the beta-aminoalcohol derivatives(10 mmol, Q = 193 C). Then, 1.1 equivalent of carbon disulfide is added.The solution was removed from the cooling bath and was allowed to reach room temperature and kept under continuous stirring for 12 hours to ensure completion of the reaction. The excess of acetonitrile was removed using a rotatory evaporator, the residue was washed with water and the product was extracted three times with diethyl ether. The organic layer was washed with 20mL of water and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was purified by column chromatography on silica gel 60 using a mixture of ethyl acetate/hexane (3:7) as the eluent. All the products were obtained as solids. They were characterized by 1H and 13C NMR spectroscopy, IR spectroscopy, EI mass spectrometry andelementary analysis.

The chemical industry reduces the impact on the environment during synthesis 40571-86-6, I believe this compound will play a more active role in future production and life.

Reference:
Article; Medini, Hayet; Mekni, Nejib Hussein; Boujlel, Khaled; Journal of Sulfur Chemistry; vol. 36; 6; (2015); p. 653 – 659;,
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Related Products of 4415-82-1, 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 4415-82-1, name is Cyclobutylmethanol. This compound has unique chemical properties. The synthetic route is as follows.

A. To a solution of cyclobutanemethanol (4.00 g, 46.4 mmol) in dichloromethane (60 mL) was added pyridine (10mL), followed by the addition of p-toluenesulfuryl chloride (7.20 g, 37.8 mmol) at 0 C. The reaction mixture wasstirred for 23 h at ambient temperature, and then diluted with diethyl ether (350 mL), washed sequentially with water,1% aqueous HCl solution, water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuoto give the product (9.00 g, 80.7%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 4415-82-1, Cyclobutylmethanol.

Reference:
Patent; Xenon Pharmaceuticals Inc.; Abreo, Melwyn; Chafev, Mikhail; Chakka, Nagasree; Chowdhury, Sultan; Fu, Jian-Min; Gschwend, Heinz, W.; Holladay, Mark, W.; Hou, Duanjie; Kamboj, Rajender; Kodumuru, Vishnumurthy; Li, Wenbao; Liu, Shifeng; Raina, Vandna; Sun, Sengen; Sun, Shaoyi; Sviridov, Serguei; Tu, Chi; Winther, Michael, D.; Zhang, Zaihui; (94 pag.)EP2316827; (2016); B1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 30379-58-9, name is Benzyl 2-hydroxyacetate, the common compound, a new synthetic route is introduced below. Safety of Benzyl 2-hydroxyacetate

To a solution of lithium 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)benzoate (theoric 0.869 mmol) and EDC (349 mg, 1.821 mmol) in dry DCM (3 ml), benzyl 2-hydroxyacetate (151 mg, 0.910 mmol) and DMAP (111 mg, 0.910 mmol) were added at RT. The final mixture was stirred for 2 days, then the solvent was evaporated, the residue was portioned between water and EtOAc, the organic layer was washed with NaHCO3 sat. sol. and brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography on silica gel (eluent: DCM/MeOH/32% NH4OH 95/5/0.5) to give 2-(benzyloxy)-2-oxoethyl 3-(cyclopropylmethoxy)-4-(N-(2-(4-methylpiperazin-1-yl)ethyl)-methylsulfonamido)benzoate as a colorless oil (370 mg, 0.661 mmol, 76% yield over 2 steps, MS/ESI+ 560.1 [MH]+)

The synthetic route of 30379-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Esposito, Oriana; Peretto, Ilaria; US2013/79313; (2013); A1;,
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Application of 6240-11-5, Adding some certain compound to certain chemical reactions, such as: 6240-11-5, name is 1-Adamantaneethanol,molecular formula is C12H20O, 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 6240-11-5.

Adamantyl acetaldehyde: To a flask containing 2-adamantyl-1-ethanol (5 g, 27.7 mmol) in CH2Cl2 (28 mL) was added TEMPO (433 mg, 2.77 mmol) followed by iodobenzene diacetate (9.8 g, 30.5 mmol). The reaction was stirred 1 hour and then diluted with CH2Cl2 (100 mL). Saturated aqueous solution of Na2S2O3 (100 mL) was added and extracted with CH2Cl2 (3×50 mL). The combined organics were washed with saturated aqueous NaHCO3 (150 mL) and brine (150 mL), dried over Na2SO4, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (5% Et2O/pentanes) to provide the title compound, which was identical to the reported literature compound (see Luly et al. (1987) J. Org. Chem. 52: 1487).

According to the analysis of related databases, 6240-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; California Institute of Technology; US2006/189830; (2006); A1;,
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Application of 34231-22-6, 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. 34231-22-6, name is 3-(Aminomethyl)benzyl Alcohol, molecular formula is C8H11NO, 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.

3-Aminomethylbenzyl alcohol (1.12 g, 8.2 mmol) was weighed into a 100 mL round bottom flask,Tetrahydrofuran (10 mL) was added and triethylamine (0.873 mL, 6.2 mmol) was added to the reaction mixture.Trifluoroacetic anhydride (0.897 mL, 6.2 mmol) was added dropwise under ice-cooling,Dropping process continued for about 30min, dropping to room temperature after stirring the reaction 3.5h,The progress of the reaction was monitored by TLC. After the reaction was completed,Adding ethyl acetate and water according to a volume of 1: 1 composition of the mixture was extracted,After the organic phase was washed with saturated ammonium chloride solution,After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure at 37 C,Purification by silica gel column chromatography, eluent ethyl acetate and petroleum ether,With gradient elution,The volume ratio of ethyl acetate / petroleum ether gradually increased from 1: 1 to 1: 2,Drying in vacuo at 37 C gave 2,2,2-trifluoro-N- (3- (hydroxymethyl) benzyl) acetamide (1.54 g,6.56 mmol) in 80% yield.

According to the analysis of related databases, 34231-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing University of Technology; Zhao Lijiao; Liu Junjun; Lai Xinxin; Song Xiuqing; Ren Ting; Zhong Rugang; (29 pag.)CN107235981; (2017); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol, the common compound, a new synthetic route is introduced below. Recommanded Product: (5-Bromo-2-chlorophenyl)methanol

[179.1] (5-Bromo-2-chlorophenyl)methanol (8.187 g) was dissolved in 100 ml of toluene, 12.2 g of diphenylposhorazide and 6.52 ml of diazabicycloundecene were added successively, and the mixture was stirred overnight at room temperature. After ethyl acetate was added thereto, the reaction mixture was successively washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column, to give 9.75 g of the title compound in the 50:1 hexane-ethyl acetate fraction.1H-NMR(CDCl3) delta: 4.48 (s, 2H) 7.28 (d, J=8.4Hz, 1H) 7.41 (dd, J=2.4, 8.4Hz, 1H) 7.56 (d, J=2.4Hz, 1H)

The synthetic route of 149965-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1394147; (2004); A1;,
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Reference of 62058-03-1, 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. 62058-03-1, name is trans-4-Aminoadamantan-1-ol. A new synthetic method of this compound is introduced below.

Example B .3 Preparation of compound 3; A mixture of 2-[(p-chlorophenyl)sulfonyl]-2-methylpropionic acid [28361-38-8] (0.00028 mol) in dichloromethane (5 ml) and DMF (5 ml) was stirred and 1-hydroxy- lH-benzotriazole (O.OOO33 mol) was added. Then the mixture was stirred for 10 minutes and iV-(ethylcarbonimidoyl)-iV,iV-dimethyl-l,3-propanediamine, monohydrochloride [25952-53-8] (O.OOO33 mol) was added. The resulting mixture was stirred for 10 minutes and (lalpha,3alpha,4alpha,5beta,7alpha) -4-aminotricyclo[3.3.1.13’7]decan-l-ol [62058-03-1] (O.OOO33 mol) was added. The reaction mixture was stirred overnight at room temperature and then the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2CyCH3OH 98/2). The product fractions were collected and the solvent was evaporated, yielding 0.094 g of compound 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62058-03-1, trans-4-Aminoadamantan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2006/24627; (2006); A2;,
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