Dimethylformamide → Dimethyl [2-(4-fluoro-2-nitrophenyl)-1-phenylethyl]malonate

Participants

Reaction Steps

A solution of benzylidene malonate (14.2 g) in DMF (280 mL) was treated with sodium hydride (2.57 g, 95%). A solution of 4-fluoro-2-nitrotoluene in DMF (10 mL) was added over 1H, and the reaction mixture was stirred at RT overnight and then quenched by the addition of glacial acetic acid (175 mL) at 0° C. A total of 500 mL of 70:30 water-methanol was added with stirring, and the organics were extracted with ethyl acetate. The organic extracts were combined and washed with saturated aqueous potassium carbonate solution (2×) and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a dark brown oil. Flash chromatography on silica gel (75:25 hexane-ethyl acetate, then 50:50 hexane-ethyl acetate) provided 7.0 g (30%) of the title compound as a red-brown solid. 1H NMR (300 MHz, CDCl3) δ 3.72 (d, 2H), 3.73 (d, 1H), 4.32 (m, 1H), 7.09-7.29 (m, 7H), 7.71 (m, 1H). MS APCI, m/z=398 (M+Na). LC/MS: 2.66 min.

Provenance & Evidence