Month: July 2021

Application of 3637-61-4, 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.3637-61-4, name is Cyclopentanemethanol, molecular formula is C6H12O, molecular weight is 100.16, as common compound, the synthetic route is as follows.

REFERENCE EXAMPLE 13 STR43 Methanesulfonyl chloride (1.52 g) was added dropwise to a solution of 1.11 g of cyclopentanemethanol and 1.50 g of triethylamine in 30 ml of dichloromethane with cooling on an ice bath over 5 minutes. The reaction mixture was stirred at room temperature for 30 minutes and then washed in sequence with three portions of water and one portion of saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2.06 g of cyclopentanemethyl methanesulfonate. NMR (CDCl3) delta: 1.1~1.9 (8H), 2.1~2.5 (1H, m), 2.02 (3H, s), 4.13 (2H, d, J=7 Hz), MS: m/z 178 (M+) STR44

The chemical industry reduces the impact on the environment during synthesis 3637-61-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamanouchi Pharmaceutical Co., Ltd.; US4987132; (1991); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 20712-12-3, 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. 20712-12-3, name is (2-Amino-5-bromophenyl)methanol. A new synthetic method of this compound is introduced below.

A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,20712-12-3, (2-Amino-5-bromophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Bifulco, JR., Neil; DiPietro, Lucian V.; Miduturu, Chandrasekhar V.; US2015/197519; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 2516-33-8, Cyclopropylmethanol, 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 Cyclopropylmethanol, blongs to alcohols-buliding-blocks compound. Safety of Cyclopropylmethanol

To a 2 L flask was charged with cyclopropanemethanol (8A) (18 g, 250 mmol, 1 equiv), TEMPO (78 mg, 0.5 mmol) and CH2Cl2 (250 mL). The solution was cooled to 0 C, and a solution of KBr (2.99 g, 25 mmol, 0.1 equiv), NaHCO3 (52.5 g, 625 mmol, 2.5 equiv), and 10-13% NaOCl (150 mL, 313 mmol, 1.25 equiv) in H2O (80 mL) was then slowly added. After the resulting mixture was had been stirring at 0 C for 45 min, the two layers were separated. The aqueous layer was back extracted with CH2Cl2 (2 x 250 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resulting residue was purified via shortpath distillation head under N2 (95-100 C) to give the corresponding aldehyde 8B (11. 02 g, 73%) as a colorless liquid.

The synthetic route of 2516-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Trost, Barry M.; Nguyen, Hien M.; Koradin, Christopher; Tetrahedron Letters; vol. 52; 17; (2011); p. 2033 – 2036;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 25125-21-7, 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.25125-21-7, name is 1-Hydroxymethyl-3-cyclopentene, molecular formula is C6H10O, molecular weight is 98.143, as common compound, the synthetic route is as follows.

1-a (Cyclopent-3-en-1-yl)methyl toluenesulfonate A mixture of (cyclopent-3-en-1-yl)methanol (1.96 g, 20 mmol) and para-toluenesulfonylchloride (3.81 g, 20 mmol) were stirred at room temperature for 2 hrs in pyridine (30 ml). After the concentration of pyridine, the reaction residues were extracted with dichloromethane, washed 1N HCl, dried with MgSO4, concentrated and separated by the column chromatography to give the desirable product (4.20 g). Yield(%): 83.2 1 H NMR(CDCl3): delta2.11(2H,m), 2.42(3H,s), 2.49(3H,m), 3.82(2H,d), 5.67(2H,s), 7.40(2H,d), 7.65(2H,d).

The chemical industry reduces the impact on the environment during synthesis 25125-21-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Samjin Pharmaceutical Co., Ltd; US5922727; (1999); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 29683-23-6 ,Some common heterocyclic compound, 29683-23-6, molecular formula is C5H10OS, 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.

INTERMEDIATE 17(2-Oxo-3 -tetrahydro-2H-thiopyran-4-yl-2,3 -dihydro- 1 H-benzimidazol- 1 -yPacetic acidStep A. fert-Butyl 2-oxo-3 -tetrahydro-2H-thiopyran-4-yl-2,3 -dihydro- 1 H-benzimidazole- 1 – carboxylateDiethyl azodicarboxylate (446 mg, 2.56 mmol) was added to a solution otert- butyl 2-oxo-2,3-dihydro-lH-benzimidazole-l -carboxylate (J Org. Chem., 1995, 60, 1565-1582) (500 mg, 2.13 mmol), triphenylphosphine (672 mg, 2.56 mmol), and tetrahydro-2H-thiopyran-4- ol (Chem. Comm., 2002, 10, 1070-1071) (303 mg, 2.56 mmol) in TetaF (10 mL). After 20 h, the reaction was concentrated in vacuo and the crude product purified by silica gel column chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 95:5, to give the title compound. MS: m/z = 335 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29683-23-6, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/130512; (2008); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 111-90-0, 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. 111-90-0, name is Diethylene Glycol Monoethyl Ether. A new synthetic method of this compound is introduced below.

[00121] Charge copper (I) iodide (FW 190.45, 0.90 grams, 4.72 mmol), 1,10-phenanthroline (FW 180.21, 0.83 grams, 4.62 mmol), cesium carbonate (FW 325.82, 19.00 grams, 58.30 mmol), 1 ,3-diiodobenzene (FW 329.90, 7.50 grams, 22.70 mmol), di(ethylene glycol) ethyl ether (FW 134.71, 14.06 grams, 104.40 mmol) and 100 milliliters of dry xylene in a 350 milliliter three necked round bottom flask. The reaction mixture was heated with stirring at reflex temperature for 20 hours under nitrogen. The resulting suspension was cooled to room temperature by adding 50 milliliters of toluene. Then the reaction mixture was filtered through celite and alumina. The low boiling (xylene and toluene) component was removed by a rotary evaporator and high boiling component di(ethylene glycol) ethyl ether by air bath oven at 180C under high vacuum for 2 hours. The residue was purified by flask chromatography on silica gel. The final dark yellow product was yielded 5.20 grams (67%). The product IR, and C NMR analysis shows the formation of aryl ether product. IR: neat (cm” FontWeight=”Bold” FontSize=”10″ ): 687, 763, 843, 995, 1058, 1 116, 1 157, 1 185, 1264, 1289, 1333, 1351, 1418, 1452, 1492, 1590, 2874. 13C NM (CDC13): 149.22, 121.87, 1 15.18, 70.84, 70.65, 69.83, 68.90, 66.5, 15.12.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111-90-0, Diethylene Glycol Monoethyl Ether, and friends who are interested can also refer to it.

Reference:
Patent; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; PATIL, Abhimanyu O.; BODIGE, Satish; WO2015/60984; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 96-35-5, Methyl 2-hydroxyacetate, 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, Product Details of 96-35-5, blongs to alcohols-buliding-blocks compound. Product Details of 96-35-5

4-(3-(3-Fluoro-4-hydroxyphenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile 1e (100 mg, 0.24 mmol) was placed in a reaction flask, followed by addition of methyl glycolate (42 mg, 0.47 mmol), triphenylphosphine (93 mg, 0.35 mmol), 5 mL of dichloromethane, and diisopropyl azodicarboxylate (72 mg, 0.35 mmol), successively. The reaction solution was stirred for 1 hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by thin layer chromatography with elution system A to obtain the title compound methyl 2-(4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluorophenoxy)acetate 31a (104 mg, yield 89.7%) as a white solid. MS m/z (ESI): 496.2 [M+1]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,96-35-5, Methyl 2-hydroxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co., Ltd.; Jiangsu Hengrui Medicine Co., Ltd.; Lu, Hejun; Sun, Piaoyang; Fei, Hongbo; Jiang, Hongjian; Wang, Haowei; Dong, Qing; US2015/225381; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 7589-27-7 ,Some common heterocyclic compound, 7589-27-7, molecular formula is C8H9FO, 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 2-(2,4-dichlorophenoxy)propanoicacid (100 mg, 0.43 mmol) in DMF (2 mL) were added 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate(HATU; 200 mg, 0.53 mmol), 2-(4-fluorophenyl)ethanol(64 lL, 0.50 mmol), and diisopropylethylamine (100 lL,0.57 mmol). The resulting mixture was stirred at room temperaturefor 2 days, then poured into water (20 mL). The aqueous mixturewas then extracted with EtOAc (20 mL 3), and the combinedorganic extracts were dried over MgSO4, filtered, and evaporated toprovide a yellow oil. The oil was subjected to flash chromatographyon silica gel with 0?30percent EtOAc/hexane. Product-containing fractionswere pooled and evaporated to provide 120 mg (75percent) ofproduct as a clear, colorless oil: Rf 0.79 (1:1 EtOAc/hexane); 1HNMR (CDCl3) d 7.37 (d, 1H), 7.12?7.05 (m, 3H), 6.95 (t, 2H), 6.64(d, 1H), 4.67 (q, 1H), 4.37?4.31 (m, 2H), 2.89 (t, 2H), 1.61 (d, 3H);m/z expected 356.0 found 356.1 (GC?MS).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7589-27-7, its application will become more common.

Reference:
Article; Williams, John D.; Torhan, Matthew C.; Neelagiri, Venugopal R.; Brown, Carson; Bowlin, Nicholas O.; Di, Ming; McCarthy, Courtney T.; Aiello, Daniel; Peet, Norton P.; Bowlin, Terry L.; Moir, Donald T.; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 1027 – 1043;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 13826-35-2, name is (3-Phenoxyphenyl)methanol, the common compound, a new synthetic route is introduced below. Recommanded Product: (3-Phenoxyphenyl)methanol

(a) 3-Phenoxybenzaldehyde Chromium trioxide (3.00 g.) was added to a stirred solution of pyridine (4.75 g.) in dry methylene chloride (75 ml.), and stirring was continued for a further 15 minutes. 3-Phenoxybenzyl alcohol (1 g.) in methylene chloride (5 ml.) was added, the mixture stirred for a further 15 minutes, decanted and the residue washed with diethyl ether (100 ml.). The filtrate was washed with 5% sodium hydroxide solution (3*50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.) and dried over Na2 SO4 to give 3-phenoxy-benzaldehyde. Alternatively the alcohol can be oxidized using Jones’ reagent, a similar yield of aldehyde being obtained.

The synthetic route of 13826-35-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National Research Development Corporation; US4464391; (1984); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 101-98-4, name is 2-(Benzyl(methyl)amino)ethanol. A new synthetic method of this compound is introduced below., HPLC of Formula: C10H15NO

EXAMPLE 3 N-Benzyl-N-methyl-ethanolamine (20.73 g), 61.94 g of toluene and 83.41 g of a 30% aqueous solution of NaOH were respectively weighed and placed in a 300-mL four-necked flask. While the mixture was stirred, the flask inside temperature was lowered to 6.8 C. Then, 31.68 g of methanesulfonyl chloride was added dropwise over 3 hours and 17 minutes at a flask inside temperature of 5 to 10 C. Water (33 mL) was added to dissolve the NaCl which had precipitated out in the aqueous phase, and the mixture was separated into the toluene phase and aqueous phase. A toluene solution of N-benzyl-N-methyl-ethanolamine methanesulfonate was thus obtained in a yield of 68.8 mole percent.

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, 101-98-4, 2-(Benzyl(methyl)amino)ethanol.

Reference:
Patent; Kano, Fumihiko; Kunihiro, Shigeki; Yoshida, Noritaka; Mori, Natsuki; US2003/162966; (2003); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts