Acetone → Ethyl(6-(1,2-dihydroxyethyl)-1-benzothiophen-3-yl)acetate

Participants

Reaction Steps

To a mixture of 4-methylmorpholine 4-oxide hydrate (527 mg), ethyl(6-vinyl-1-benzothiophen-3-yl)acetate (320 mg), acetone (0.5 mL), CH3CN (0.500 mL) and water (0.500 mL) was added osmium(VIII) oxide (7% microcapsule, 472 mg) at room temperature. The mixture was stirred at room temperature for 4 d. The insoluble material was removed by filtration through Celite®, and the filtrate was concentrated in vacuo. Water was added to the mixture and the mixture was extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (200 mg).

Provenance & Evidence