Sodium hydride → Diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate

Participants

Reaction Conditions

Reaction Steps

0.6 g (14.92 mmol) of sodium hydride is added in portions to a solution of 4.13 g (12.43 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 40 ml of DMF at 0° C. The reaction solution is then allowed to reach room temperature and is stirred for 1 hour. The reaction solution is then cooled again to 0° C., 3.9 g (13.68 mmol) of tert-butyl 4-(2-bromoethyl)benzoate in 10 ml of DMF are added, and the mixture is stirred at this temperature for 30 min. The mixture is then stirred at room temperature overnight. The reaction mixture is added to ice-water and extracted three times with ethyl acetate, and the combined organic phases are washed with saturated brine and dried over sodium sulphate. After filtration, the solvent is evaporated to dryness in vacuo, and the resulting crude product is purified by preparative HPLC. 933 mg (1.7 mmol, 14% yield) of a colourless solid are obtained.

Provenance & Evidence