Dimethyl Sulfoxide → 2-Acetyl-6-methylpyridine

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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, 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%).

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