Benzaldehyde → HCID 68565974, compound

Participants

Reaction Conditions

Reaction Steps

Under cooling (0° C.), diethyl methylmalonate ([609-08-5], 1.175 g, 7 mmol) was added to a suspension of NaH (60% in mineral oil, 325 mg, 8 mmol) in diethyl ether (30 ml). After 3 h at r.t, the solvent was evaporated and the residue was dissolved in DMF (20 ml). To this solution, triphenylvinylphosphonium bromide ([5044-52-0], 3.00 g, 8 mmol) and benzaldehyde ([100-52-7], 860 mg, 8 mmol) were added. The reaction mixture was stirred at 100° C. overnight, and was then taken up in ethyl acetate, washed (H2O), and dried (Na2SO4). The solvent was evaporated, and 2-methyl-2-(3-phenyl-allyl)-malonic acid diethyl ester was isolated from the residue by column chromatography (silica gel, ethyl acetate/heptane). MS: m/e=291.0 [M+H+].

Provenance & Evidence