Formic Acid → 2-[4-(Methoxycarbonyl)benzyl]-4-[4-(methoxycarbonyl)phenyl]butanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 40 g (80.9 mmol) of diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate, 1.49 g (5.67 mmol) of triphenylphosphine and 363 mg of palladium acetate in 500 ml of dioxane is mixed at room temperature with a solution of 37.2 ml (267 mmol) of triethylamine and 7.6 ml (202 mmol) of formic acid in 100 ml of dioxane. The reaction mixture is then stirred at 110° C. overnight. After conversion is complete, the reaction solution is cooled, and the solvent is removed in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 20.98 g (56.6 mmol, 70% of theory) of a colourless solid are obtained.

Provenance & Evidence