反应详情

温度

130 °C

A screw-capped tube equipped with a magnetic stir bar is charged with m-anisaldehyde (3.04 mL, 25 mmol), methyl acrylate (4.50 mL, 50 mmol), (PPh3)3RhCl (1.16 g, 1.25 mmol), 2-amino-3-picoline (1.06 mL, 10 mmol), and benzoic acid (702 mg, 5 mmol). The reaction mixture is stirred at 130° C. for 3 days. After cooling to room temperature, the resulting mixture is dissolved in diethyl ether and ished with water and brine. The organic phase is then dried over Na2SO4 and concentrated. The residue is then purified on silica gel (10-30% ethyl acetate in hexane) to give methyl 4-(3-methoxyphenyl)-4-oxobutanoate (5.02 g, 90%) as a clear reddish brown oil. 1H NMR (CDCl3, 400 MHz) δ 7.57 (d, J=9.5 Hz, 1H), 7.51 (dd, J=3.0, 2.0 Hz, 1H), 7.38 (t, J=10.0 Hz, 1H), 7.12 (ddd, J=10.5, 3.5, 1.0 Hz, 1H), 3.85 (s, 3H), 3.71 (s, 3H), 3.32 (t, J=8.5 Hz, 2H), 2.77 (t, J=8.5 Hz, 2H).

1. customA screw-capped tube equipped with a magnetic stir bar
2. temperatureAfter cooling to room temperature
3. dry with materialThe organic phase is then dried over Na2SO4
4. concentrationconcentrated
5. customThe residue is then purified on silica gel (10-30% ethyl acetate in hexane)