Dimethyl Sulfoxide → 3-(4-Fluorophenyl)-3-methylbutyraldehyde

Participants

Reaction Steps

12 mL of a 2 M solution of oxalyl chloride in dichloromethane was diluted with 19 mL of dichloromethane and cooled on a dry ice/acetone bath. To this solution was added a dropwise a solution of 3.6 mL of DMSO in 16 mL of dichloromethane. After 10 minutes, a solution of 3-(4-fluorophenyl)-3-methylbutan-1-ol (3.6 g, 19.8 mmol) in 12 mL of dichloromethane was added and the mixture was stirred for 15 minutes. 14 mL of triethylamine was then added, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature and was quenched with water and diluted with hexanes. The organic layer was separated, washed with water, dried, filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel (eluent: hexanes to hexanes-dichloromethane (9:1), gradient) to give 1.2 g of 3-(4-fluorophenyl)-3-methylbutyraldehyde as an oil.

Provenance & Evidence