Dimethyl Sulfoxide → HCID 12972211, compound

Participants

Reaction Conditions

Reaction Steps

A solution of alcohol 5 (10 g, 45 mmol) and dichloromethane (200 mL) at −30° C. was treated dropwise with oxalyl chloride (4.92 g, 24 mL, 0.275 mol). The reaction was stirred at −30° C. for 30 min, cooled to −60° C., and DMSO (6.4 mL) was added slowly over 15 min. The reaction was stirred for one hour, cooled to −78° C. for 30 min, and then treated dropwise with triethylamine (40 mL). The reaction was warmed to room temperature and stirred for 1 hr, followed by the addition of water and dichloromethane with thorough mixing. The organic layer was separated, dried with MgSO4, filtered and the solvent was evaporated to an oil. Purification of this material using flash chromatography (flash silica, 70/30: hexane/EtOAc) afforded 6 as a white crystalline solid.

Provenance & Evidence