Diethyl Malonate → HCID 18349838, compound

Participants

Reaction Steps

117 mg (4.9 mmol) of sodium hydride (80% in oil) and 15 ml of THF are introduced into a round-bottomed flask under a stream of nitrogen. 540 μl (3.6 mmol) of diethyl malonate are then added dropwise and the mixture is stirred until the evolution of gas has ceased. This solution is introduced dropwise into a mixture of 1.4 g (3.24 mmol) of allyl (E)-2-[3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)acryloyloxy]benzoate, 20 ml of THF and 187 mg of tetrakis(triphenylphosphine)palladium(0) and stirred at room temperature for three hours. The reaction medium is poured into water and extracted with ethyl ether, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (95/5). After evaporating the solvents, 800 mg (63%) of (E)-2-[3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)acryloyloxy]benzoic acid, with a melting point of 137-8° C., are collected.

Provenance & Evidence