Category: alcohols-buliding-blocks

Synthetic Route of 96-35-5, 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 96-35-5, name is Methyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of KOtBu (996.6 mg, 8.881 mmol) in THF (640.4 mg, 8.881 mmol) cooled to 0 C was added dropwise methyl 2-hydroxyacetate (675.7 mu, 8.881 mmol) and stirred for 10 minutes. The acrylonitrile (589.1 mu, 8.881 mmol) was then added and the reaction stirred at ambient temperature. After 3 hours, the reaction was diluted with H20 (50 mL), then extracted with Et20 (25 mL) to remove any starting ester. The basic aqueous phase was acidified with 2M HC1 (5 mL), then extracted with Et20 (2 x 50 mL). The combined organic phases were dried with MgS04, filtered, and concentrated to afford a light brown oil (446 mg, 45.2% yield). 1H NMR (CDC13) delta 4.63 (t, 1H), 4.24 (t, 1H), 4.14 (d, 1H), 4.02 (d, 1H), 3.57 (t, 1H).

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 96-35-5, Methyl 2-hydroxyacetate.

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BLAKE, James F.; BRANDHUBER, Barbara J.; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; XU, Rui; WINSKI, Shannon L.; WO2014/78328; (2014); A1;,
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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. 27646-80-6, name is 2-Methyl-2-(methylamino)propan-1-ol. A new synthetic method of this compound is introduced below., Formula: C5H13NO

A slurry of the product of example 81a (215 mg) in dichloromethane (2 ml) was treated with oxalylchloride solution (400 mul 2M in dichloromethane). A drop of DMF was added. The mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, and redissolved in dichloromethane (2 ml). This solution was treated with 2-methyl-2-methylamino-propan-l-ol (175 mg; prepared in a similar manner as described by S. G. Kuznetsov, A.V. Eltsov, J. Gen. Chem. USSR, 32, 502 (1962)) and stirred for 1 h at room temperature. The reaction mixture was poured into an aqueous NaHCOs solution (5percent) and was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with heptane/ethyl acetate to provide crystalline material.Yield: 80 mg. Mp 114-1160C; LC/MS-ESI: [M+H]+ = 476.5; hFSHRago (CHO luc) EC50 = 6.0 nM

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 27646-80-6, 2-Methyl-2-(methylamino)propan-1-ol.

Reference:
Patent; N.V. ORGANON; WO2009/98283; (2009); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 148043-73-6, name is 4,4,5,5,5-Pentafluoropentan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C5H7F5O

Into a reactor (internal capacity: 200 mL, made of glass) equipped with a stirrer and a dropping funnel, C2F5CH2CH2CH2OH (23.6 g), triethylamine (16.1 g) and acetone (80 mL) were put and stirred. Then, by an ice bath, the inner temperature of the reactor was adjusted to be at most 10 C., and in a nitrogen atmosphere, a solution of 4-(chloromethyl)benzoic acid chloride (25.0 g) in acetone (15 mL) was dropwise added. Further, the temperature was returned to room temperature, and stirring was continued for 2 hours. (0156) The obtained reaction crude liquid was transferred to a separating funnel, AK-225 (100 mL) was added, followed by washing three times with distilled water (100 mL), and the solvent in the AK-225 phase was distilled off to obtain 40.2 g of a compound (A-2) (pale yellow liquid) represented by the following structural formula (A-2) and classified into the above compound (A). The yield was 93%. (0157) (0158) The measured results of 1H-NMR and 19F-NMR of the obtained fluorinated compound (A-2) are shown below. 1H-NMR (solvent:CDCl3) delta(ppm): 2.05-2.31 (4H, m, -CH2[CH2CH2]CF2-), 4.41 (2H, t, -OCH2-), 4.62 (2H, s, ClCH2-), 7.48 (2H, d, Ph), 8.03 (2H, d, Ph). 19F-NMR (solvent:CDCl3) delta(ppm): -85.9 (3F, s, -CF3), -118.7 (2F, t, -CF2-). (0161) Into a reactor (internal capacity: 50 mL, made of glass) equipped with a stirrer and a dropping funnel, methacrylic acid (2.73 g), potassium carbonate (5.02 g) and DMF (20 mL) were put and stirred. Then, heating was carried out so that the inner temperature of the reactor became 50 C., and a solution of the compound (A-2) (10.0 g) in DMF (10 mL) was dropwise added. The dropping funnel was replaced with a Dimroth condenser, and the reactor was heated to 80 C. and stirred for 2 hours. (0162) The obtained reaction crude liquid was transferred to a separating funnel, AK-225 (50 mL) was added, followed by washing three times with distilled water (50 mL), and the solvent in the AK-225 phase was distilled off to obtain 11.1 g of a fluorinated compound (I-5) of the present invention (pale yellow liquid) represented by the following structural formula (I-5). The yield was 97%. The measured results of 1H-NMR and 19F-NMR of the obtained fluorinated compound (I-5) of the present invention are shown below. 1H-NMR (solvent:CDCl3) delta(ppm): 1.99 (3H, s, -CH3), 2.05-2.31 (4H, m, -CH2[CH2CH2]CF2-), 4.40 (2H, t, -COO[CH2]CH2-), 5.26 (2H, s, -COO[CH2]Ph-), 5.63 (1H, s,transC?CH2), 6.19 (1H, s,cisC?CH2), 7.46 (2H, d, Ph), 8.04 (2H, d, Ph). (0166) 19F-NMR (solvent:CDCl3) delta(ppm): -85.9 (3F, s, -CF3), -118.8 (2F, t, -CF2-).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 148043-73-6, 4,4,5,5,5-Pentafluoropentan-1-ol.

Reference:
Patent; Asahi Glass Company, Limited; Hoshino, Taiki; US8471056; (2013); B2;,
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Adding a certain compound to certain chemical reactions, such as: 25392-41-0, 4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

The crude product (2 g, 9.50 mmol) in 200 mL single neck flask, adding 1 n naoh (100ml) the concentrated solution immediately turned yellow, and the solution was placed in an oil bath and heated to reflux for 2 h, and after the reaction, cooling to room temperature, with concentrated sulfuric acid to adjust the pH to 2 -3, and the resulting solution with ethyl acetate (30 ml × 4) the extraction, combining the organic phase with saturated saline (20 ml × 2, washed, dried over anhydrous sodium sulfate, filtered Solvent, the filtrate is evaporated under reduced pressure to obtain gray-brown columnar crystalline 1.3 g, the crude yield 71.2% of the crude product (1 g, 5.20 mmol) suspended in 10 mL of methanol and added dropwise 0 5 Ml of concentrated sulfuric acid, after dropping, heating under reflux to react for about 4 h, after the reaction, the methanol was removed under reduced pressure, the residual liquid is poured into 30 ml of water, in ethyl acetate (20 ml × 3) extraction, combining the organic phase with saturated sodium bicarbonate solution (15 mL × 2) washing, saturated brine (15 mL × 2, washed, dried over anhydrous sodium sulfate, filtered, the filtrate is decompressed and evaporated to obtain an yellow-brown oil, column chromatography (petroleum ether/ethyl acetate, 80: 20 Purification, v/v) to obtain light yellow solid 0.75 g, 70% yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound,25392-41-0, 4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; ChinaPharmaceutical University; Huang, Wenlong; QIAN, Hai; Li, Zheng; YANG, Jianyong; Su, Xin; Pan, MiaoBo; (22 pag.)CN105566267; (2016); A;,
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Reference of 480449-99-8, 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. 480449-99-8, name is Benzyl 3-hydroxycyclobutanecarboxylate. A new synthetic method of this compound is introduced below.

REFERENTIAL EXAMPLE 153 Benzyl 3-methoxycyclobutanecarboxylate: Methyl iodide (194 mul) and silver oxide (237 mg) were added to a solution of the compound (317 mg) obtained in Referential Example 151 in N,N-dimethylformamide (3.0 ml), and the mixture was stirred at 45 C. for 1 hour. Methyl iodide (194 mul) and silver oxide (226 mg) were additionally added to the reaction mixture, and the mixture was stirred at 45 C. for 16 hours. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate_hexane=1:10) to obtain the title compound (152 mg). 1H-NMR (CDCl3) delta: 2.14-2.24(2H,m), 2.44-2.54(2H,m), 2.59-2.72(1H,m), 3.21(3H,s), 3.73-3.81(1H,m), 5.11(2H,s), 7.22-7.39(5H,m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,480449-99-8, its application will become more common.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; US2005/20645; (2005); A1;,
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Application of 83647-43-2, 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 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Dioxane (200 mL) was charged to a 500 mL round-bottom flask and nitrogen was bubbled through for 10 minutes. (3-bromo-2-methylphenyl)methanol (9.0 g, 44.8 mmol) was added and nitrogen was bubbled through for 10 minutes. Potassium acetate (13.18 g, 134 mmol) was added and nitrogen was bubbled through for 10 minutes. Bis(pinacolato)diboron (18.19 g, 71.6 mmol) was added and nitrogen was bubbled through for 10 minutes. PdCl2(dppf)-CH2Cl2 (4.75 g, 5.82 mmol) was added and nitrogen was bubbled through for 10 minutes. The reaction was heated at 80 C overnight. The reaction was diluted with ethyl acetate (200 ml) , filtered through a celite bed and the bed washed with ethyl acetate. The combined organic portions were concentrated under vacuum to provide a black pasty residue. This crude residue was adsorbed onto silica gel and chromatographed on a 120 g silica gel column using acetone in petroleum ether. The product eluted at 5.0 % acetone. Fractions containing the product were combined and the solvent was removed under vacuum. An off-white solid was obtained. The solid was stirred with petroleum ether and filtered under vacuum to remove boron impurities. The title compound (8.7g, 77%) was pure by NMR analysis. 1H NMR (500MHz, DMSO-de) delta 7.33 (dd, J=0.9, 7.5 Hz, 1H), 7.45 (d, J=6.9 Hz, 1H), 7.22 (t, J=7.5 Hz, 1H), 4.73 (d, J=3.0 Hz, 2H), 2.58 (s, 3H), 1.58 (br. s., 1H, OH), 1.37 (s, 12H).

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 83647-43-2, (3-Bromo-2-methylphenyl)methanol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHUPAK, Louis S.; ZHENG, Xiaofan; WO2015/34820; (2015); 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. 13674-16-3, name is Methyl 2-hydroxy-3-phenylpropanoate, molecular formula is C10H12O3, 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. Computed Properties of C10H12O3

Step 6 (2R)-2-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxy]3-phenyl-propionic acid methyl ester To a solution of 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenol (5.0 g, 12.1 mmol), (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (3.3 g, 18.3 mmol), and triphenylphosphine (4.8 g, 18.3 mmol) in anhydrous benzene (50 mL) at room temperature under nitrogen was added dropwise diethyl azodicarboxylate (2.6 mL, 18.3 mmol) over a period of 25 min. The reaction mixture was heated for 2 h, then stirred at room temperature for 3 days. The crude reaction mixture was adsorbed onto silica gel and chromatographed twice with petroleum ether:ethyl acetate (95:5) to yield the title compound as a white foamy solid (4.5 g, 65%): NMR (DMSO-d6): delta8.18 (d, 1H), 7.64 (ddd, 1H), 7.53-7.43 (m, 2H), 7.38-7.24 (m, 5H), 7.00 (s, 2H), 4.80 (t, 1H), 3.58 (s, 3H), 3.31 (m, 2H), 2.42 (s, 3H), 2.24 (s, 3H), 2.19 (s, 3H), 1.55 (s, 3H); MS(EI): [M+], 1 bromine isotope pattern, 572/574; Anal. Calc. for C32H29BrO3S: C, 67.01; H, 5.10; N, 0.00. Found: C, 66.33; H, 5.09; N, 0.09; Analytical HPLC indicates a major component (94.39%).

With the rapid development of chemical substances, we look forward to future research findings about 13674-16-3.

Reference:
Patent; American Home Products Corporation; US6251936; (2001); B1;,
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Synthetic Route of 4415-82-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 4415-82-1 as follows.

To a suspension of sodium hydride (60% dispersion in mineral oil, 37 mg, 0.93 mmol) in THF (1 mL) was added cyclobutanemethanol (86 mu^, 0.91 mmol) at room temperature. A solution of compound 94 (200 mg, 0.46 mmol) in THF (3.5 mL) was added at room temperature. The mixture was stirred at room temperature for 30 min, at 50 C for 2 h, and cooled to room temperature. Aq. sat. NaHCCb was added. The mixture was extracted with EtOAc. The organic extract was dried withNa2SC>4, and concentrated. The residue was purified by flash chromatography (silica gel, eluting with 0% to 50% EtOAc in hexanes) to give compound 213 (203 mg, 91 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4415-82-1, its application will become more common.

Reference:
Patent; REATA PHARMACEUTICALS, INC.; JIANG, Xin; BENDER, Christopher, F.; VISNICK, Melean; HOTEMA, Martha, R.; SHELDON, Zachary, S.; LEE, Chitase; CAPRATHE, Bradley, William; BOLTON, Gary; KORNBERG, Brian; (497 pag.)WO2018/111315; (2018); A1;,
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Electric Literature of 41175-50-2 , The common heterocyclic compound, 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, molecular formula is C12H15NO, 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 aldehyde 7 (300 mg, 0.428 mmol) in propionic acid (5 mL) was added 8-hydroxyjulolidine (161 mg, 0.856 mmol, 2 eq) and PTSA (8 mg, 0.042 mmol, 0.1 eq). The solution was protected from light and stirred at room temperature overnight. To the brown mixture was added a solution of chloranil (103 mg, 0.428 mmol, 1 eq) in DCM (10 mL), the reaction turned dark and was allowed to stir overnight at room temperature. The dark purple solution was evaporated to dryness. The residue was purified by column chromatography on silica gel (gradient of 100% DCM to 9/1 DCM/Methanol) to obtain 130 mg of 8 (30%) as a purple solid after lyophilisation (dioxane/water: 1/1). Rf=0.32 (DCM/MeOH, 9/1). 1H-NMR (300 MHz, CDCl3): delta 7.84 (d, J = 8.1 Hz, 1H, H Ar), 7.06 (d, J = 7.9, 1H, H Ar), 6.97-6.86 (m, 5H, H Ar, H7), 6.71 (d, J = 2.9 Hz, 1H, H Ar), 4.47-4.40 (m, 4H, CH2O), 4.21 (s, 4H, NCH2COOMe), 4.11 (s, 4H, NCH2COOMe), 3.87 (t, J = 6.1 Hz, 2H, CH2O), 3.67 (s, 6H, 2 OMe), 3.56 (m, 14H, 2 OMe, H1, H4), 3.11 (d, J = 7.0 Hz, 2H, CH2N3), 3.04 (t, J = 6.3 Hz, 4H, H6), 2.75 (q, J = 6.2 Hz, 4H, H3), 2.13-2.10 (m, 4H, H5), 2.00 (t, J = 5.5 Hz, 4H, H2), 1.49-1.34 (m, 4H, CH2), 1.19-1.03 (m, 4H, CH2). 13C-NMR (75 MHz, CDCl3): delta 171.97 (CO ester), 171.56 (CO ester), 153.04 (C Ar), 152.74 (C Ar), 152.31 (C Ar), 152.09 (C Ar), 151.02 (C Ar), 150.43 (C Ar), 144.79 (C Ar), 139.41 (C Ar), 138.16 (C Ar), 132.61 (C Ar), 128.20 (CH Ar), 127.15 (CH Ar), 126.33 (CH Ar), 123.34 (C Ar), 122.64 (CH Ar), 122.61 (CH Ar), 121.91 (CH Ar), 119.54 (CH Ar), 113.89 (C Ar) (CH Ar), 113.43 (C Ar), 113.35 (C Ar), 105.16 (C Ar), 69.10 (CH2O), 67.70 (CH2O), 67.19 (CH2O), 53.66 (NCH2COOMe), 53.52 (NCH2COOMe), 51.73 (4 OMe), 51.16 (CH2N3), 50.97 (C1 or C4), 50.52 (C1 or C4), 28.82 (CH2), 28.73 (CH2), 27.72 (C3), 26.26 (CH2), 25.52 (CH2), 20.83 (C2), 20.00 (C6), 19.85 (C5). MS (ES+), calcd for C57H68N7O12 [M]+ 1042.5, found 1042.9. HRMS (ES+), calcd for C57H68N7O12 [M]+ 1042.4920, found 1042.4949.

The synthetic route of 41175-50-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Paris Sciences et Lettres – Quartier Latin; Mallet, Jean-Maurice; Collot, Mayeul; EP2878602; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3236-48-4, trans-1,4-Cyclohexanedimethanol, 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, Safety of trans-1,4-Cyclohexanedimethanol, blongs to alcohols-buliding-blocks compound. Safety of trans-1,4-Cyclohexanedimethanol

Example 1.106: Preparation of Sodium 2-(((lr,4r)-4-(((4- Chlorophenyl)(phenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetate.; Method 1.; Step A: Preparation of ((lr,4r)-4-(hydroxymethyl)cyciohexyI)methyl 4- chlorophenyl(phenyl)carbamate.; 4-Chloro-N-phenylaniline (15.0 g, 73.6 mmol), tribasic potassium phosphate, (fine powder, 4.69 g, 22.1 mmol), N^V-carbonyldiimidazole (13.14 g, 81 mmol) and acetonitrile (75 mL) were charged to a 500-mL, jacketed, four-necked cylindrical reaction flask equipped with a mechanical stirrer and a condenser. The reaction mixture was heated at 65 0C under nitrogen and monitored by HPLC. After about 2.5 h HPLC showed > 98% conversion to the intermediate N-(4-chlorophenyl)-N-phenyl-lH-imidazole-l-carboxamide. After about 5.5 h a solution of (lr,4r)-cyclohexane-l,4-diyldimethanol (37.2 g, 258 mmol) in acetonitrile (150 mL) at 65 0C was added to the reaction mixture over 20 min. The resulting mixture was heated at 65 0C overnight. etaPLC showed about 98% conversion to the required product. The mixture was filtered, and the cake was rinsed with acetonitrile (2 x 25 mL). The filtrate was concentrated under reduced pressure (40 0C, 32 torr) 124.125 g of distillate was collected. The residue was diluted with water (50 mL) and this mixture was concentrated under reduced pressure (400C, 32 torr) and 35.184 g of distillate was collected. The residue was diluted with water (50 mL) and the resulting mixture was allowed to stir overnight to give a white paste. The mixture was filtered, and the cake was rinsed with 25% acetonitrile/water (2 x 75 mL). The solid was dried in a vacuum oven to leave a white solid (22.271 g); 94.8% purity by etaPLC peak area. LCMS m/z = 374.3 [M+eta]+; 1H nuMR (400 MHz, DMSO-^6) delta ppm 0.77 – 0.93 (m, 4 H) 1.23 (dd, J = 6.22, 3.51 Hz, 1 H) 1.47 (dd, J = 6.32, 2.91 Hz, 1 H) 1.56 – 1.76 (m, 4 H) 3.20 (t, J= 5.78 Hz, 2 H) 3.92 (d, J = 6.13 Hz, 2 H) 4.33 (t, J = 5.31 Hz, 1 H) 7.28 – 7.35 (m, 5 H) 7.38 – 7.47 (m, 4 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3236-48-4, trans-1,4-Cyclohexanedimethanol, and friends who are interested can also refer to it.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/117095; (2009); A1;,
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