Dimethyl Sulfoxide → HCID 19600233, compound

Participants

Reaction Steps

To a solution of 4.27 g (33.6 mmol) of oxalyl chloride in 100 ml of dichloromethane, 4.78 ml (67.3 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 6.580 g (22.431 mmol) of 4-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-ylsulfonyl)benzyl alcohol in 50 ml of dichloromethane was added at -78° C., followed by stirring for 15 minutes. To this mixture, 18.8 ml (135 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. After the reaction mixture was washed with water, the water layer was re-extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1 to 2/1) to yield the desired product.

Provenance & Evidence