Water → Methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-formyl-1-benzothiophen-3-yl)acetate

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Reaction Steps

To a mixture of methyl(6-((2,6-dimethylpyridin-3-yl)methoxy)-4-vinyl-1-benzothiophen-3-yl)acetate (459 mg), CH3CN (2 mL), water (2 mL) and acetone (2 mL) were added osmium(VIII) oxide (7% microcapsule, 907 mg) and NMO (439 mg) at room temperature. The mixture was stirred at room temperature for 20 h. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo. The residue was poured into aqueous solution of Na2S2O3 at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. To a mixture of the residue, THF (3 mL) and water (3 mL) was added sodium periodate (802 mg) at 0° C. The mixture was stirred at room temperature for 1 h. The mixture was quenched with aqueous solution of Na2S2O3 at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine twice, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (293 mg).

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