Ethyl cyanoacetate → (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

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Reaktionsschritte

Potassium phosphate (0.751 g, 3.54 mmol) was added to a solution of ethyl 2-cyanoacetate (2.00 g, 17.68 mmol) and 4-phenoxybenzaldehyde (3.50 g, 17.68 mmol) in ethanol (50 mL). After 1 h at room temperature, the mixture was quenched with water (20 mL). The ethanol solvent was evaporated in vacuo. The residue was taken up in ethyl acetate (150 mL), washed with brine (2×10 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 5 to 20% ethyl acetate in hexanes, gave (E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate as tan liquid. 1H NMR (500 MHz, CDCl3) δ ppm 8.19 (1H, s), 7.92-8.05 (2H, m), 7.37-7.48 (2H, m), 7.24 (1H, t, J=7.42 Hz), 7.10 (2H, δ, J=7.70 Hz), 6.98-7.07 (2H, m), 4.38 (2H, q, J=7.15 Hz), 1.40 (3H, δ, J=7.15 Hz); MS (ES+) m/z: 294 (M+H); LC retention time: 4.405 min (analytical HPLC Method B).

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