Dimethyl Sulfoxide → 2-(N-allyloxycarbonyl-N-benzylamino)acetaldehyde

Participants

Reaction Steps

To a solution of oxalyl chloride (13.8 ml) in dichloromethane (270 ml) was added dropwise a solution of dimethyl sulfoxide (19.7 ml) in dichloromethane (30 ml) below -60° C. under atmosphere of nitrogen. After stirring the mixture at the same condition for 30 minutes, a solution of 2-(N-allyloxycarbonyl-N-benzylamino)ethanol (32.6 g) in dichloromethane (30 ml) was added to the mixture below -60° C. with stirring. After 30 minutes, triethylamine (58 ml) was added to the mixture at the same condition. The mixture was stirred below -60° C. for 30 minutes and the reaction temperature was allowed to rise to ambient temperature. The mixture was washed with water (300 ml), 1N hydrochloric acid (300 ml×2), saturated aqueous sodium hydrogen carbonate (300 ml), and brine (300 ml) successively, dried over magnesium sulfate, and concentrated under reduced pressure to give 2-(N-allyloxycarbonyl-N-benzylamino)acetaldehyde (32.9 g) as a syrup.

Provenance & Evidence