Dimethylformamide dimethyl acetal → Ethyl 2-(3-fluoro-4-nitrobenzoyl)-3-(dimethylamino)acrylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

N,N-Dimethylformamide dimethyl acetal (100 g, 810 mmol) was added dropwise (10 min) to a cooled (0° C.) solution of ethyl 3-(3-fluoro-4-nitrophenyl)-3-oxopropanoate (138 g, 540 mmol) in toluene (540 mL). The reaction was warmed (50° C.) for 2.5 h and then the volatiles were evaporated under reduced pressure to afford the desired product (167 g, 100%), which was sufficiently pure (>95% by NMR) to proceed without further purification. 1H NMR (300 MHz, DMSO-d6) δ 8.24-8.29 (m, 1H), 7.92 (s, 1H), 7.60-7.74 (m, 1H), 7.58-7.62 (m, 1H), 3.97 (q, J=7.0 Hz, 2H), 3.44 (s, 3H), 2.81 (s, 3H), 0.99 (t, J=7.0 Hz, 3H); ES-MS m/z 310.9 (MH)+; HPLC RT (Method B) 2.87 min.

Herkunft & Nachweise