Potassium Carbonate → 3-(3-Epoxymethoxyphenyl)thieno[2,3-d]isoxazole

Participants

Reaction Steps

A mixture of 28 g of 3-(3-hydroxyphenyl)thieno[2,3-d]isoxazole, 23 g of epibromohydrin and 30 g of milled potassium carbonate in 40 ml of dimethylformamide and 40 ml of acetonitrile was stirred under nitrogen at 90°-100° C. until completion of reaction. The reaction was complete after 4 hours and allowed to cool to room temperature. Quenching with water (400 ml), extracting with 50/50 ether/ethyl acetate soluiton (3×400 ml), and washing with water (2×400 ml) were conducted. The organics were dried over anhydrous magnesium sulfate and the solvents were evaporated to give an oil. The oil was purified by HPLC (4:1 hexane/ethyl acetate) to yield 23.3 g of a solid with a melting point of 88°-90° C.

Provenance & Evidence