m-Chloroperbenzoic acid → Methyl 9-(3,3-dimethyloxiran-2-YL)-7-methyl-3-oxonon-6-enoate

Participants

Reaction Conditions

Reaction Steps

A solution of 5.1 g of m-chloroperbenzoic acid in 50 ml of methylene chloride was added dropwise at -40° C. under a nitrogen atmosphere to a solution of 6 g of the product of Example 3 in 60 ml of methylene chloride and after stirring for 15 minutes at -20° C., the mixture was poured into a saturated aqueous sodium bicarbonate solution. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium bicarbonate solution and then with water, dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and was eluted with a 7-3 benzene-ethyl acetate mixture to obtain 3.1 g of methyl 10-epoxy-7,11-dimethyl-3-oxo-6-dodecenoate in the form of a colorless liquid with a refractive index nD25 = 1.4680.

Provenance & Evidence