Dimethyl Sulfoxide → HCID 86607429, compound

Participants

Reaction Conditions

Reaction Steps

A DCM solution of oxalyl chloride (4.38 mL, 2.0 M 8.76 mmol) was diluted with dry DCM (50 mL) and cooled to −78° C. then a solution of DMSO (0.76 mL, 10.77 mmol) in DCM (5 mL) was added dropwise. After 15 min., a solution of methyl 5-[3-(2-(hydroxymethyl)-5-oxopyrrolidin-1-yl)propyl]thiophene-2-carboxylate (2.0 g, 6.73 mmol) in DCM (10 mL) was added dropwise to this solution. The resulting solution was stirred at −78° C. for 2 hours. Et3N (4.7 mL, 33.65 mmol) was added and the solution warmed to RT. After 15 min. the solution was diluted with DCM (100 mL) and washed with a saturated solution of NH4Cl (2×100 mL), brine (100 mL), dried over sodium sulfate and concentrated in vacuo to afford the aldehyde intermediate (1.95 g, 98%) used in the next step without further purification.

Provenance & Evidence