Dimethyl Sulfoxide → 5-(Difluoromethyl)furan-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution containing 6.5 cm3 of DMSO (dimethyl sulphoxide) and 60 cm3 of methylene chloride is added at -60° C. under a nitrogen atmosphere to a solution containing 3.84 cm3 of oxalyl chloride and 40 cm3 of methylene chloride. The reaction mixture is maintained under agitation at -60° C. and 3.6 g of 5-difluoromethyl 2-furanmethanol in solution in 30 cm3 of methylene chloride is added. Agitation takes place for 2 hours at -60° C. and a solution of 16.1 cm3 of triethylamine and 30 cm3 of methylene chloride is added over 15 minutes. The reaction mixture is maintained under agitation for half an hour at -60° C., then the temperature is allowed to rise to -20° C. and agitation is continued at this temperature for half an hour. It is poured into a solution of sodium acid phosphate, extracted with methylene chloride and dried. 3.6 g of product is obtained which is chromatographed on silica eluting with a hexane--ethyl-acetate mixture 8-2. After chromatography 2.5 g of desired product is obtained.

Provenance & Evidence