Dimethyl Sulfoxide → (+/-)-trans-3-[2-(2-Chloro-phenyl)-5,7-dimethoxy-4-oxo-4h-chromen-8-yl]-1-methyl-pyrrolidine-2-carbaldehyde

Participants

Reaction Steps

Dimethyl sulfoxide (1.8 mL, 25.3 mmol) in methylene chloride (20 mL) was added to a stirred solution of oxalyl chloride (840 μL, 9.84 mmol) in dry methylene chloride (120 mL) dropwise at −50° C. The reaction mixture was stirred for 30 min. Compound of example 7, (2.0 g, 4.65 mmol) in methylene chloride (20 mL) was added dropwise to the reaction mixture. The resulting mixture was further stirred for 30 min. Triethylamine was added dropwise at −50° C. and the reaction mixture was warmed to room temperature and basified with NaHCO3 solution (10 mL). Reaction mixture was extracted with methylene chloride, organic layer was washed with water, brine and dried (anhydrous Na2SO4) to afford the title compound.

Provenance & Evidence