Uses
Diethyl diallylmalonate is the starting material for enantioselective synthesis of carbocyclic nucleoside analogues. It is also used as Low catalyst loading in ring-closing metathesis reaction. Cationic nickel (with monodentate phosphoramidites and Wilkes azaphospholene as ligands) catalyzed cycloisomerisation of diethyl diallylmalonate has been reported.
Definition
ChEBI: Diethyl diallylmalonate is a fatty acid ester.
General Description
Low catalyst loading in ring-closing metathesis reaction of diethyl diallylmalonate has been reported. Cationic nickel (with monodentate phosphoramidites and Wilke′s azaphospholene as ligands) catalyzed cycloisomerisation of diethyl diallylmalonate has been reported.
Synthesis
To a mixture of diethyl malonate (10 g, 62.5 mmol) and allyl bromide (14.25 g, 187.5 mmol), a concentrated solution of sodium ethanolate (70 mL ethanol solution of 8.6 g sodium) was slowly added between 5-10C with continuous stirring. After the addition of sodium ethoxide, the reaction mixture was stirred at the same temperature for another 1 h. The cold water bath was then removed and the mixture was stirred at room temperature overnight. The excess solvent was removed and the residue was added to water and extracted with ethyl acetate. The organic phase was dried over Na2SO4 and evaporated to give a light yellow liquid. The crude substance was purified by vacuum distillation to give a colorless liquid.
