Water → 2-(2-Phenylethyl)oxirane

Participants

Reaction Steps

3-Phenylpropionaldehyde (26.8 g) is added under nitrogen to the ylide prepared from trimethylsulfoxonium iodide (48.4 g) and sodium hydride (55% dispersion in oil; 9.6 g) in dry dimethylsulfoxide (200 ml), according to the procedure in J. Am. Chem. Soc., 84, 867 (1962) and ibid., 87, 1353 (1965). After one hour, the solution was poured into 1 liter of water and the product extracted with ether (3×300 ml.). The, extract was washed with water (2×150 ml.) dried (MgSO4) and evaporated to give an oil 1,2-epoxy-4-phenylbutane, used directly in the next step.

Provenance & Evidence