Dimethyl Sulfoxide → 2,5-Hexanedione

Participants

Reaction Steps

To a solution of dimethylsulfoxide (1.56 g, 20.0 mmoles) and oxalyl chloride (1.9 g, 15.0 mmoles) in 20 ml of methylene chloride cooled to -78° C. was added 1.67 g (10.0 mmoles) of 3-(2,5-dimethylpyrrol-1-yl)-2-butanol obtained by dehydration cyclization of 3-amino-2-butanol and acetonylacetone in acetic acid. One hour later, 3 ml of triethylamine was added, and the mixture stirred at room temperature for 5 hours. The mixture was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, and concentrated, and chromatographed on a column of silica gel using cyclohexane/ethyl acetate (4/1) as an eluent to afford 3-(2,5-dimethylpyrrol-1-yl)-2-butanone (990 mg, 6.0 mmoles, 60%).

Provenance & Evidence