Dimethyl Sulfoxide → HCID 10961270, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (579 mg, 4.56 mmol) in CH2Cl2 (15 mL) at -70° C. there was slowly added DMSO (711 mg, 9.12 mmol). The mixture was stirred for 3 minutes, then at -70° C. there was slowly added a solution of the alcohol from Step 5 (1.7 g, 3.8 mmol) in CH2Cl2 (15 mL). The resulting mixture was stirred at -70° C. for 20 minutes, then there was slowly added Et3N (1.92 g, 19 mmol). The mixture was stirred in the cold for a further 5 minutes, then it was allowed to warm up to room temperature. After dilution with Et2O (200 mL) the mixture was washed twice with 1N HCl, then with H2O (3×), dried and evaporated to a residue which was chromatographed on silica gel, eluting with a 1:1 mixture of hexane and EtOAc, to afford the title compound as a thick oil.

Provenance & Evidence