Dimethyl Sulfoxide → N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

A solution of oxalyl chloride (878 mg) in dichloromethane (5 mL) was cooled to -78° C. and was treated dropwise with a solution of dimethyl sulfoxide (595 mg) in dichloromethane (2 mL). The resulting mixture was stirred at -78° C. for 15 minutes, and was treated dropwise with a solution of N-[2-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methylbenzamide (1.22 g) in dichloromethane (10 mL)/dimethyl sulfoxide (2 mL). The mixture was stirred at -78° C. for 1 hour, was treated with triethylamine (1.75 g), warmed to room temperature and stirred for 1 hour. The mixture was then poured into water and extracted with dichloromethane. The organic extract was washed (water, brine), dried, filtered through activated magnesium silicate [Florisil (trademark)] and evaporated to afford the aldehyde as a pale yellow oil (1.18 g); MS: m/z=350[(M+1), 35Cl2 ].

Provenance & Evidence