Monoethyl malonate → HCID 18791132, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in hexane (2.5M, 146 ml) was added dropwise to a mechanically stirred solution of ethyl hydrogen malonate (24.3 g, 0.18 ml) in dry tetrahydrofuran (210 ml) cooled to -60° C. under nitrogen atmosphere. After addition, the reaction mixture was stirred at -10° C. for 10 minutes then cooled to -60° C. and a solution of 3-cyanomethylcyclobutanecarbonyl chloride (17.0 g, 0.11 ml) in dry tetrahydrofuran (230 ml) added dropwise at such a rate to maintain temperature below -10° C. The reaction mixture was stirred overnight at room temperature, diluted with aqueous hydrochloric acid (2M, 180 ml) and extracted with diethyl ether (2×200 ml). The combined extracts were washed with a saturated solution of sodium bicarbonate (100 ml), water (100 ml) and brine solution (100 ml), dried, filtered and evaporated to a yellow oil (20.5 g). The crude product was purified by chromatography eluting with diethyl ether-hexane (1:1 and then 3:2) to give the title compound as an oil.

Provenance & Evidence