Potassium Carbonate → 2-(2-Phenylethyl)oxirane

Participants

Reaction Conditions

Reaction Steps

A modified procedure of Woodward was used (Bernier, D. et al., The Journal of Organic Chemistry 2008, 73, 4229). A stirred solution of 4-phenyl-1-butene 62 (500 mg, 568 μl, 3.78 mmol) in CH2Cl2 (20 ml) was cooled to 0° C. m-CPBA (816 mg, 4.73 mmol) was added as a solid and the reaction mixture was stirred at 0° C. for 1.5 h, then r.t. for 24 h. The reaction mixture was poured into saturated K2CO3 solution (50 ml) and extracted with CH2Cl2 (2×50 ml). The combined organic phases were washed with saturated K2CO3 solution (50 ml) before being dried (MgSO4), filtered and concentrated to give a clear colourless liquid. This material was purified by column chromatography, eluting with petrol/EtOAc (9:1), to give the epoxide 61 (10.2 g, 91%) as a clear colourless liquid. The 1H, 13C, and IR data were consistent with the literature (Mitchell, J. M. et al., Journal of the American Chemical Society 2001, 123, 862; Elings, J. A. et al., European Journal of Organic Chemistry 1999, 1999, 837).

Provenance & Evidence