5-Benzyloxyindole → 3-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester

Participants

Reaction Steps

A mixture of 5-benzyloxy-1H-indole (4.46 g, 20.0 mmol), phenyl-propionic acid ethyl ester (7.00 g, 40.0 mmol), and tetrabutylammonium fluoride [1.0 M in THF] (36.0 mL, 50.0 mmol) was stirred for 3 days. After removal of solvent, the crude reaction mixture was submitted to flash chromatography on silica gel with ethyl acetate/hexane (1:4) to give the title compound (5.42 g, 68% yield) as an E/Z isomeric mixture. Mass Spectrum (LCMS, ESI) calculated for C26H24NO3 398.2 (M+H); found 398.2.

Provenance & Evidence