Ethanol → 2-[4-(trifluoromethoxy)phenyl]oxirane

Participants

Reaction Steps

To a suspension of sodium hydride(1.54 g, 38.46 mmol) in 35 mL of dry DMSO was added, via a solid addition funnel, trimethylsulfoxonium iodide (7.84 g, 35.61 mmol) over 5 minutes. After H2 gas evolution ceases the cloudy solution was treated with a solution of 4-trifluoromethoxybenzaldehyde (4.96 g, 25.05 mmol) in 35 mL of THF over 15 minutes. After one hour, 1 mL of ethanol was slowly added, then the THF and ethanol were removed by rotary evaporation. The DMSO solution was poured into 100 mL of water and then extracted with dichloromethane(3×75 mL). The combined organic extracts were washed with dilute brine (2×75 mL), dried (Na2SO4), filtered, evaporated and purified by flash chromatography (silica gel, 10% ethyl acetate/hexane). This procedure afforded 1.95 g of the title compound as a colorless oil.

Provenance & Evidence