Allyl bromide → 2-Allyl-2-ethylmalonic acid diethyl ester

Participants

Reaction Steps

To a stirred solution of diethyl ethylmalonate (43.0 mL, 0.228 mol) in THF (500 mL) at 0° C. was added sodium hydride (60%; 9.2 g, 0.228 mol) in portions. The mixture was warmed to rt and stirred at rt for 75 min, and was added allyl bromide (23.9 mL, 0.275 mol). The reaction was stirred at rt for 4 h, and then cooled to 0° C. and quenched with water (400 mL) and 6 N hydrochloric acid (80 mL). The product was extracted with diethyl ether (4×200 mL), and the extracts were washed with brine (2×200 mL), dried over sulfate and concentrated. The residue was distilled to give 2-allyl-2-ethylmalonic acid diethyl ester (b.p. 89-91° C./ca. 2 mm Hg).

Provenance & Evidence