Dimethyl Sulfoxide → HCID 21055337, compound

Participants

Reaction Conditions

Reaction Steps

0.61 ml (0.007 mol) of oxalyl chloride and 20 ml of dichloromethane are introduced into a round-bottomed flask kept under an inert atmosphere. The mixture is cooled to −78° C. and then 1 ml (0.014 mol) of dimethyl sulfoxide is introduced. After stirring at −78° C. for 15 minutes, 1.5 g (0.007 mol) of 2-(S)-methyl-3-(2-methoxyphenylthio)propan-1-ol (XXb-1), in solution in 15 ml of dichloromethane, are added dropwise. The mixture is stirred at −78° C. for 1 hour and then 2 ml (0.014 mol) of triethylamine are added. After 15 minutes at −78° C., the mixture is reheated to −10° C. and stirred at this temperature for 45 minutes. The aldehyde is not isolated at this stage but is used in situ in the following reductive amination reaction.

Provenance & Evidence