Diethyl Malonate → HCID 18007487, compound

Participants

Reaction Steps

A solution of diethyl malonate (5.14 g, 32.1 mmol) in anhydrous ethyl alcohol (100 mL) was reacted with 96% sodium ethoxide (2.28 g, 32.2 mmol) at 76° C. for 1 h. After the solution cooled to room temperature, (2-bromoethoxy)-tert-butyldimethylsilane (7.68 g, 32.1 mmol) was added. The resulting solution was heated at 76° C. for 15.5 h and then concentrated. The residue was partitioned between dichloromethane and water. The organic layer was dried (Na2SO4) and concentrated to give the title compound as a brown oil (10.22 g, 100%). 1H NMR (CDCl3) δ 4.19-4.11 (m, 4H), 3.62 (t, 2H, J=6.0 Hz), 3.55 (t, 1H, J=7.3 Hz), 2.10-2.06 (m, 2H), 1.23 (t, 6H, J=7.1 Hz), 0.85 (s, 9H), 0.01 (s, 6H).

Provenance & Evidence