반응 #52283

반응 방정식

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

→

title compound

수율 96.0%

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

수율 96.0%

용매

methanol

반응 조건

후처리

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

실험 절차

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.

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