m-Chloroperbenzoic acid → HCID 54469068, compound

Participants

Reaction Steps

13.54 g of 3-chloro-perbenzoic acid (MCPBA, 70%) was dissolved in 30 ml of CH2Cl2 and cooled to 0°. 8.84 g of (E)-(S)-5,9-dimethyl-deca-2,8-dienoic acid ethyl ester dissolved in 15 ml of CH2Cl2, was slowly added and the mixture kept for an additional 0.5 h in the ice bath. The reaction was then quenched by pouring onto crushed ice/sodium pyrosulfite, extracted twice with AcOEt, washed with 2N NaOH, water and brine, dried over sodium sulfate and evaporated to dryness to yield 9.59 g of (5R)-7-((RS)-3,3-dimethyl-oxiranyl)-5-methyl-hept-2-enoic acid ethyl ester as 1/1 epimeric mixture, sufficiently pure for the next step.

Provenance & Evidence