Reacción #52283

Ecuación de reacción

3-(5-benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester

→

title compound

Rendimiento 96.0%

3-(5-Hydroxy-indol-1-yl)-3-phenyl-propionic acid ethyl ester

Rendimiento 96.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter removal of the catalyst
2. 2
   Filtraciónby filtration
3. 3
   Otrothe crude product was purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1)

Procedimiento

A mixture of 3-(5-benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester (1.94 g, 4.89 mmol) and palladium on carbon [10% w/w] (60 mg) in methanol (25 mL) was stirred under hydrogen atmosphere for 24 h. After removal of the catalyst by filtration, the crude product was purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1) to give the title compound in 96% yield. 1H NMR (CDCl3) δ 7.10-7.30 (m, 7H), 6.99 (d, J=2.4 Hz, 1H), 6.69 (dd, J=2.4 and 8.7 Hz, 1H), 6.39 (d, J=3.2 Hz, 1H), 5.99 (t, J=7.6 Hz, 1H), 5.31 (br, 1H), 4.03 (q, J=7.2 Hz, 2H), 3.26 (m, 2H), 1.08 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3) δ 170.4, 149.7, 139.8, 131.5, 129.3, 128.8, 127.9, 126.2, 125.8, 111.6, 110.6, 105.2, 101.4, 61.1, 56.2, 40.4, 13.9. Mass Spectrum (LCMS, ESI) calculated for C19H20NO3 310.1 (M+H); found 310.1.

Fuente