Diethyl Malonate → Propanedioic acid, (2-methyl-2-propenyl)-, dimethyl ester

Participants

Reaction Steps

To a solution of diethyl malonate (2.30 g) in THF (20 mL) was added 60% sodium hydride (592 mg) at 0° C., and the mixture was stirred for 1 hr. 3Bromo-2-methylpropene (2.00 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 20 hr. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.60 g) as a colorless oil.

Provenance & Evidence