Diethyl Malonate → HCID 13113430, compound

Participants

Reaction Conditions

Reaction Steps

The oil was removed from 21.70 g (0.542 mol) of 60% sodium hydride in oil by washing with hexanes. To the residue suspended in 200 ml tetrahydrofuran, 84.38 ml (0.556 mol) diethyl malonate was added slowly via addition funnel. While the reaction was cooled to −35 to −10° C., 100 g (0.400 mol) of 2,3-dibromopropene was added slowly via addition funnel. After heating to reflux for 1 hour, the reaction was cooled to room temperature and concentrated ill vacuo. Hexanes and water were added to the residue and the resulting mixture was transferred to a separatory funnel where the-phases were separated. The isolated organic layer was washed with IN hydrochloric acid then dried over magnesium sulfate and filtered. The solvent was removed from the filtrate in vacuo to yield 154 g of 2-(2-bromo-allyl)-malonic acid diethyl ester as an oil.

Provenance & Evidence