HCID 11773223, compound → HCID 86757618, compound

Participants

Reaction Conditions

Reaction Steps

Methyl (2-(2-propenyl)-3-(2-tetrahydropyranyloxyethyl)benzofuran-7-yloxy)acetate (0.97 g) and osmium tetroxide (0.07 M solution in t-butyl alcohol, 0.37 ml) were dissolved in dioxane/water (3:1) and the solution was cooled to 0° C. To this solution, sodium periodate (1.38 g) was added for 10 minutes. After stirring the reaction solution at 0° C. for 30 minutes, the solution was stirred at room temperature for additional 30 minutes. The reaction solution was filtered through Celite and the precipitate was washed with THF (12 ml). The filtrate was cooled to 0° C. and sodium borohydride (98 mg) was added, followed by stirring the resultant for 40 minutes. The reaction solution was poured into water (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1)using silica gel to obtain the desired compound (412 mg, yield: 42%).

Provenance & Evidence