Acetone → HCID 20484851, compound

Participants

Reaction Steps

3.00 g of ethyl 2-(1-methyl-ethylidene)-3-oxo-butanoate [described in Helv. Chim. Act., Vol. 54 (1971), p. 1797] were added dropwise at room temperature to a suspension of 860 mg of sodium hydride as a 50% mineral oil suspension in 50 ml of tetrahydrofuran and the mixture was refluxed for one hour and then cooled to room temperature. 13 ml of a solution of 1.6 M of butyllithium in hexane were added to the mixture at 0° C. and the mixture was stirred at 0° C. for 30 minutes. The mixture was cooled to -10° C. and 1.60 ml of acetone were added thereto. The mixture was poured into water and the mixture was extracted with ether. The ether phase was washed with aqueous saturated sodium chloride solution, dried over magnesium sulfate and evaporated to about 100 ml to obtain a solution of ethyl 5-hydroxy-5-methyl-2-(1-methyl-ethenyl)-3-oxo-hexanoate and its isomer, ethyl 5-hydroxy-5-methyl-2-(1-methyl-ethenyl)-3-oxo-hexanoate.

Provenance & Evidence