Dimethyl malonate → HCID 66757258, compound

Participants

Reaction Steps

Small portions of NaH (60%, 7.92 g, 198 mmol) are added to a solution of dimethyl malonate (22.6 ml, 198 mmol) in DMSO (100 mL) at 0° C. The ice bath is removed and the mixture stirred at room temperature for 2 hours. The solution is rechilled to 0° C. and a solution of 2-bromo-1-phenyl-hexan-1-one (2–1) (16.8 g, 66 mmol) in DMSO (50 mL) is added slowly. The ice bath is removed and the mixture stirred overnight. Water (500 mL) is added and the mixture is extracted with EtOAc (4×150 mL). The combined extracts are washed with brine (300 mL), dried (Na2SO4), and evaporated, to provide the product as a light yellow oil. LC-MS (M+1) 307. 1H NMR (δ, CDCl3) 7.98–8.02 (m, 2H), 7.46–7.60 (m, 3H), 4.18–4.28 (m, 1H), 4.03–4.12 (m, 1H), 3.80 (s, 3H), 3.6.1 (s, 3H), 1.55–1.63 (m, 2H), 1.02–1.20 (m, 4H), 0.76 (t, J=0.72 Hz, 3H).

Provenance & Evidence