Dimethyl Sulfoxide → N,N-diethyl-4-formylbenzamide

Participants

Reaction Steps

Oxalyl chloride (10.8 ml) was dissolved in dichloromethane (260 ml), added with dimethyl sulfoxide (17.5 ml) at −78° C. under an argon gas flow and stirred at the same temperature for 5 minutes. The reaction mixture was added with a solution of 4-diethylcarbamoylbenzyl alcohol (12.80 g) dissolved in dichloromethane (260 ml) at −78° C. and further stirred at the same temperature for 30 minutes. The reaction mixture was added with triethylamine (43.1 ml) at −78° C. and further stirred at room temperature for 30 minutes. After the reaction mixture was added with water (500 ml) and the layers were separated, the aqueous layer was extracted with dichloromethane (500 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 12.075 g of the title compound. Yield: 95%.

Provenance & Evidence