Dimethyl Sulfoxide → HCID 21278446, compound

Participants

Reaction Steps

27 ml of a 1M solution of oxalyl chloride in methylene chloride were cooled to -60° C. and 13.5 ml of a 1M solution of dimethyl sulfoxide in methylene chloride were added. After stirring for 5 minutes, a solution of 1.09 g of 3-hydroxymethyl-1-(2-propynyl)-1H-pyrrole-2-carbonitrile in 20 ml of methylene chloride was added, and the temperature was kept at -60° C. for 2 hours. 70 ml of a 1M solution of triethylamine in methylene chloride were added with stirring for 10 minutes at -60° C., and the temperature was allowed to rise to 20° C. 20 ml of water were added, followed by stirring, decanting and concentrating to dryness. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (6-4) to obtain 456 mg of 3-formyl-2-cyano-1-(2-propynyl)-1H-pyrrole.

Provenance & Evidence