* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -75℃; for 1.33333 h; Stage #2: With triethylamine In dichloromethane at -75 - 20℃; for 2 h;
To a -75°C solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at-75°C for 10 min, and then slowly treated with a solution of [1- (6-] methyl-pyridin-2-yl) -ethanol (28 [G,] 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1. [02 MOL, 5APOS;EQUIV).] The resulting, mixture was warmed to [20° OVER] 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3: 1 hexanes/ethyl acetate) yielded [1- (6-METHYL-PYRIDIN-2-YL)-ETHANONE] (25.36 g, 92percent).
With triethylamine In dichloromethane; dimethyl sulfoxide
Step B Preparation of 1-(6-Methyl-pyridin-2-yl)-ethanone To a -75° C. solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at -75° C. for 10 min, and then slowly treated with a solution of 1-(6-methyl-pyridin-2-yl)-ethanol of Step A (28 g, 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1.02 mol, 5 equiv). The resulting mixture was warmed to 20° over 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3:1 hexanes/ethyl acetate) yielded the title compound (25.36 g, 92percent).
Reference：
[1] Patent: US2004/176390, 2004, A1,
3
[ 71777-66-7 ]
[ 5308-63-4 ]
Reference：
[1] Organic Magnetic Resonance, 1982, vol. 20, # 4, p. 242 - 248
To a -75C solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at-75C for 10 min, and then slowly treated with a solution of [1- (6-] methyl-pyridin-2-yl) -ethanol (28 [G,] 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1. [02 MOL, 5'EQUIV).] The resulting, mixture was warmed to [20 OVER] 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3: 1 hexanes/ethyl acetate) yielded [1- (6-METHYL-PYRIDIN-2-YL)-ETHANONE] (25.36 g, 92%).
With triethylamine; In dichloromethane; dimethyl sulfoxide;
Step B Preparation of 1-(6-Methyl-pyridin-2-yl)-ethanone To a -75 C. solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at -75 C. for 10 min, and then slowly treated with a solution of 1-(6-methyl-pyridin-2-yl)-ethanol of Step A (28 g, 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1.02 mol, 5 equiv). The resulting mixture was warmed to 20 over 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3:1 hexanes/ethyl acetate) yielded the title compound (25.36 g, 92%).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
