Diethyl Malonate → Diethyl allylmalonate

Participants

Reaction Steps

To a THF suspension (50 ml) containing sodium hydride (0.92 g, 21 mmol, 55% in oil) was added dropwise at 0° C. diethyl malonate (3.2 g, 20 mmol). The reaction liquid was heated to room temperature and stirred for 1 hour. The reaction liquid was stirred overnight together with allyl bromide (2.9 g, 24 mmol). With water added, the reaction liquid was extracted with ether. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After solvent removal, the residues were purified by silica gel chromatography. Thus there was obtained 2.88 g of diethyl allylmalonate (yields: 72%). This product was identical with commercial one.

Provenance & Evidence