Cesium carbonate → Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate

Participants

Reaction Steps

A solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF is mixed at room temperature with 62.66 g (192 mmol) of caesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6]. The mixture is then stirred at room temperature overnight. After conversion is complete, the reaction solution is evaporated to dryness, and the residue is taken up in water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated brine and dried over sodium sulphate. After filtration, the solvent is evaporated to dryness in vacuo. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). 41.35 g (83.6 mmol, 65% of theory) of a colourless solid are obtained.

Provenance & Evidence