Water → ethyl(2E)-3-(2-fluoro-4-methoxyphenyl)acrylate

Participants

Reaction Steps

To a solution of ice-cooled ethyl diethylphosphonoacetate (9.45 g, 42.1 mmol) in tetrahydrofuran (50 mL) was added sodium hydride (60% in oil, 1.54 g, 38.5 mmol) and the mixture was stirred for 15 min. A solution of 2-fluoro-4-methoxybenzaldehyde (5.00 g, 32.4 mmol) in tetrahydrofuran (30 mL) was added dropwise. The mixture was stirred at room temperature for 2 hr, and water was added. The mixture was extracted with ethyl acetate. The extract washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title compound (7.07 g, yield 97%) as a colorless oil. 1H NMR (CDCl3) δ: 1.33 (3H, t, J=7.1 Hz), 3.83 (3H, s), 4.26 (2H, q, J=7.1 Hz), 6.41 (1H, d, J=16.2 Hz), 6.61-6.73 (2H, m), 7.45 (1H, t, J=8.6 Hz), 7.75 (1H, d, J=16.2 Hz).

Provenance & Evidence