Potassium Carbonate → [2-(1-Benzyl-1H-pyrazol-4-yl)-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone

Participants

Reaction Steps

This compound was prepared by application of the general procedure to 2-iodo-5-methoxy-phenol, 1-benzyl-4-ethynyl-1H-pyrazole and 3,4,5-trimethoxy-iodo-benzene. The crude product was stirred with potassium carbonate (excess) in methanol to hydrolyse ester by-products and submitted to silica-gel flash chromatography (eluent=2:1 hexanes:ethyl acetate) to afford the title compound as a yellow resin that crystallised after trituration in diethyl ether (31% yield). An analytical sample was obtained by preparative thin layer chromatography (eluent=2:1 hexane:ethyl acetate). 1H-NMR (CDCl3) δ 8.10 (s, 1H), 8.03 (s, 1H), 7.36-7.21 (m, 5H), 7.13 (d, J=8.7 Hz, 1H), 7.11 (s, 2H), 7.03 (d, J=2.0 Hz, 1H), 6.79 (dd, J 8.7, 2.0 Hz, 1H), 5.29 (s, 2H), 3.92 (s, 3H), 3.85 (s, 3H), 3.75 (s, 6H). 13C-NMR (CDCl3) δ 190.3, 158.2, 154.3, 153.3, 153.0, 142.4, 139.3, 135.7, 133.7, 130.3, 128.9, 128.3, 127.8, 121.8, 120.9, 114.0, 113.1, 112.3, 107.1, 95.6, 61.1, 56.4, 56.3, 55.8.

Provenance & Evidence