Dimethyl Sulfoxide → HCID 19599952, compound

Participants

Reaction Steps

To a solution of 1.07 g (8.44 mmol) of oxalyl chloride in 50 ml of dichloromethane, 1.20 ml (16.9 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 1.650 g of the above crude 4-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-ylsulfonyl)benzyl alcohol in 10 ml of dichloromethane was added at -78° C., followed by stirring for 15 minutes. To this mixture, 4.70 ml (33.7 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. The reaction mixture was diluted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (dichloromethane) and crystallized from diethyl ether-hexane to yield the desired product.

Provenance & Evidence