Diethyl Ether → HCID 13300907, compound

Participants

Reaction Steps

100 mg of pyridinium chlorochromate and 200 mg of Molecular Sieves 3A were suspended in 6 ml of dry methylene chloride. While the suspension was cooled with ice and stirred, a solution of 50 mg of the product obtained in step 5, in a small amount of methylene chloride, was added. The temperature was elevated to room temperature, and the reaction mixture was allowed to react for 6 hours under vigorous agitation. After 10 ml of ether were added to the reaction mixture, the mixture was filtered using 15 g of "Florisil", and the precipitate and the "Florisil" were washed well with ether. The filtrate and the washing solution were combined and were evaporated to dryness to provide a crude product. Using n-hexane-ethyl acetate as an eluent, the crude product was subjected to column chromatography using 3 g of alumina (activity: II). The fraction which eluted with n-hexane-ethyl acetate (99:1) was recovered and was evaporated to dryness to provide 42 mg of purified (3S,4E,8R,9R)-8-epoxy-3-isopropyl-6-methylene-10-oxo-4-cyclodecen-1-one (the compound of formula 8). The yield was 85%.

Provenance & Evidence