Sulfuric Acid → 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane

Participants

Reaction Steps

A solution of 0.26 g of methanesulfonic acid (2S,3S)-3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-hydroxy-4-phenylbutyl ester in 1.6 ml of tetrahydrofuran is treated at -15° with a solution of 0.090 g of potassium tert.butylate in 0.5 ml of tetrahydrofuran and the mixture is stirred for 0.5 hours. The mixture is treated with 2.2 ml of semi-saturated sodium chloride solution and the pH value is adjusted to 6 with 0.1 ml of 1N sulphuric acid. Thereafter, the mixture is extracted with ethyl acetate. The extracts are dried and filtered, and the filtrate is evaporated to give 0.12 g (60%) of 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane, IR (KBr): 1773 m and 1709 s (C=O of imide).

Provenance & Evidence