Dimethyl Sulfoxide → HCID 13917420, compound

Participants

Reaction Steps

Dimethyl sulfoxide (0.27 ml; 3.81 mmol) was added at -78° C. in an argon atmosphere to 5 ml of a dichloromethane solution of 0.17 ml (1.95 mmol) of oxalyl chloride, and the mixture was stirred for 10 minutes under the same conditions. To the resulting solution was added 3 ml of a dichloromethane solution o 432 mg (0.94 mmol) of 1α,3β-diacetoxychol-5-en-24-ol (1), and the mixture was further stirred for 15 minutes. Triethylamine (1.05 ml; 7.55 mmol) was added to the reaction mixture, and the mixture was stirred for 5 minutes. The temperature of the reaction mixture was returned to ambient temperature. It was treated in a customary manner (extracted with ether). The crude product was purified by silica gel column chromatography [30 g; eluted with hexane/ethyl acetate (5:1)] to give 382 mg of the captioned aldehyde (2).

Provenance & Evidence