Diethyl Malonate → Diethyl allylmalonate

Participants

Reaction Steps

A 500 mL three necked round bottom flask was charged with diethyl malonate (20 g), dry potassium carbonate (43 g) and dry CH3CN (200 mL) under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 10 minutes and allylbromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80° C. for 24 hours. The reaction mixture was cooled to room temperature and filtered through celite bed. The celite bed was washed with acetonitrile (100 mL) and the combined filtrate was concentrated to give diethyl 2-allylmalonate (24 g) as colorless liquid. 1H NMR (CDCl3): δ 1.26 (t, 6H), 2.61-2.67 (m, 2H), 3.42 (t, 1H), 4.20 (q, 4H), 5.03-5.16 (m, 2H), 5.70-5.85 (m, 1H).

Provenance & Evidence