تفاعل #52283

معادلة التفاعل

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

→

title compound

المردود 96.0%

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

المردود 96.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر