Diethyl allylmalonate

Chemical properties

clear colorless to slightly yellow liquid

The Uses of Diethyl allylmalonate

Diethyl allylmalonate is an important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals, agrochemicals and flavors and fragrances compounds.

Preparation

Diethyl allyl malonate is obtained by reacting diethyl malonate with allyl bromide.
Under nitrogen atmosphere, to a 500 mL three-neck round bottom flask was added diethyl malonate (20 g), anhydrous potassium carbonate (43 g) and anhydrous CH3CN (200 mL). The reaction mixture was stirred at room temperature for 10 minutes, then allyl bromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80°C for 24 hours. The reaction mixture was cooled to room temperature and filtered through a bed of celite. The celite bed was washed with acetonitrile (100 mL) and the combined filtrates were concentrated to give diethyl allylmalonate (24 g) as a colorless liquid.

Synthesis Reference(s)

Chemistry Letters, 17, p. 291, 1988
The Journal of Organic Chemistry, 28, p. 504, 1963 DOI: 10.1021/jo01037a058