Phenol → (2R)-2-(Phenoxymethyl)oxirane

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Reaction Steps

Add phenol (1.089 g, 11.572 mmol) to a slurry of sodium hydride (0.347 g, 14.465 mmol) in N,N-dimethylformamide (77.1 mL) and stir at room temperature for 40 minutes. Add 3-nitrobenzenesulfonic acid (R)-1-oxiranylmethyl ester (3.00 g, 11.572 mmol) and stir at room temperature for 16 hours (J. Org. Chem., 54, 1296-1304 (1989). Quench with saturated aqueous ammonium chloride (75 mL), dilute with water (75 mL) and extract with diethyl ether (3×300 mL). Combine the organic extracts, wash with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous ammonium chloride (200 mL), dry (magnesium sulfate), filter and purify (silica gel chromatography, eluting with 10:90 to 50:50 ethyl acetate:hexanes) to give the desired compound as a clear liquid (1.410 g, 81.1%).

Provenance & Evidence