Ethyl Acetoacetate → HCID 86735725, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.742 g of ethyl acetylacetate in 5 ml of tetrahydrofuran was slowly added to a mixture of 672mg of sodium hydride in a 50% oil mixture in 10 ml of tetrahydrofuran cooled to 0° C and the mixture was held at 0° C for 30 minutes. 8.7 ml of 1.6N butyllithium in hexane was added dropwise at 0° C to the reaction mixture and after standing at 0° C for 30 minutes, the mixture was cooled to -60° C. A solution of 2.3 g of the product of Step B in 5 ml of anhydrous tetrahydrofuran was added to the mixture and the mixture was held at -60° C for 3 hours and then overnight at -20° C. The mixture was poured into an iced monosodium phosphate solution and was extracted with ethyl acetate. The extracts were washed, dried and evaporated to dryness to obtain a yellow oil residue. The latter was chromatographed over silica gel and was eluted with an 80-20-2 cyclohexane-ethyl acetate-triethylamine mixture to obtain 1.47 g of ethyl (6E) 8,9-epoxy-3-oxo-6-nonenoate in the form of an oil.

Provenance & Evidence