Dimethyl Sulfoxide → HCID 20464723, compound

Participants

Reaction Steps

To a solution of dimethylsulfoxide (390 mg, 5 mmol) in methylene chloride (25 ml) under N2 cooled to -78° C. is added a solution of oxalyl chloride (630 mg, 5 mmol) in methylene chloride (2 ml). The mixture is allowed to stir at -78° for 30 minutes, then a solution of ethyl 1-methyl-2-hydroxymethyl)-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate (1.63 g, 5 mmol) in CH2Cl2 (5 ml) is added. The resulting solution is stirred for 1 hour, then triethylamine (500 mg, 5 mmol) is added. The reaction is followed by TLC until complete. The resulting solution is washed with water (2×25 ml) then saturated brine, and dried over anhydrous sodium sulfate. The crude product is purified by preparative HPLC to afford ethyl 1-methyl-2-formyl-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate.

Provenance & Evidence