Water → HCID 11600896, compound

Participants

Reaction Steps

To a solution of (5-dimethylamino-benzo[b]thiophen-2-yl)-methanol (790 mg, 3.8 mmol) and triethylamine (4.9 mL, 35.1 mmol) in dimethyl sulfoxide (20 mL) was added a solution of pyridine-sulfur trioxide (1.8 g, 11.2 mmol) in dimethyl sulfoxide (20 mL). The mixture was stirred for 1 hour at room temperature followed by addition of water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with water (3×50 mL) and brine (2×50 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a colourless oil that was purified by flash chromatography (10:90:1 to 50:50:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give a solid that was recrystallised from ethanol to give the title compound (743 mg, 95%) as a solid, mp 105-106° C.

Provenance & Evidence