반응 #168222

반응 방정식

Potassium phosphate

ethyl 2-cyanoacetate

4-phenoxybenzaldehyde

→

(E)-ethyl 2-cyano-3-(4-phenoxyphenyl)acrylate

용매

ethanol

반응 조건

후처리

1. 1
   기타the mixture was quenched with water (20 mL)
2. 2
   기타The ethanol solvent was evaporated in vacuo
3. 3
   세척washed with brine (2×10 mL)
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated
6. 6
   세척eluting with 5 to 20% ethyl acetate in hexanes

실험 절차

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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