Реакция #52283

Уравнение реакции

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

→

title compound

Выход 96.0%

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

Выход 96.0%

Растворители

methanol

Условия реакции

Обработка

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

Методика

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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