Diethyl Malonate → HCID 70843787, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.8 g, 0.077 mol) was suspended in N,N-dimethylformamide (150 mL) at 0° C. Diethyl malonate (9.9 g, 0.0623 mol) was added in three portions and the resulting suspension was stirred at 0° C. for 10 min. A solution of 2-(bromomethyl)-1-chloro-3-nitrobenzene (147-1; 13 g, 0.0519 mol) in N,N-dimethylformamide (150 mL) was added drop wise. The reaction mixture was stirred for 45 min at 0° C., then diluted with saturated ammonium chloride and extracted with ethyl acetate (2×250 mL). The combined organics were dried over anhydrous sodium sulphate and concentrated to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.762-7.741 (d, J=8.4 Hz, 1H), 7.635-7.616 (d, J=7.6 Hz, 1H), 7.365-7.324 (t, J=8.4 Hz, 1H), 4.195-4.142 (q, J=7.2 Hz, 4H), 3.817-3.779 (t, J=7.6 Hz, 1H), 3.675-3.656 (d, J=7.6 Hz, 2H), 1.236-1.201 (t, J=7.2 Hz, 6H).

Provenance & Evidence