m-Chloroperbenzoic acid → 4,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose

Participants

Reaction Steps

To a solution of 3-allyl-4-methyl-pent-4-en-2-one (20.0 g) in methylene chloride (100 ml) was added dropwise a solution of m-chloroperbenzoic acid (29 g) in methylene chloride (300 ml) at 0° to 5° C. The reaction mixture was stirred at 0° to 5° C. for 3 hours and then at 20° C. overnight. The reaction solution was progressively washed with an aqueous sodium hydrogen carbonate solution, aqueous sodium sulfite solution, aqueous sodium hydrogen carbonate solution and then with an aqueous sodium chloride solution. After removing the solvent by evaporation, the residue was distilled to obtain 7.2 g of the unreacted material and 5.2 g of the objective 3-allyl-4-methyl-4,5-epoxy-pentan-2-one.

Provenance & Evidence