1,3-Dichlorobenzene → 3-Methyl-4-allyloxy-7-(2-thienoyl)benzofuran

Participants

Reaction Steps

A solution of 3-methyl-4-allyloxy-7-(2-thienoyl)benzofuran (0.43 g, 1.44 mmol) in 1,3-dichlorobenzene (4 mL) was heated to reflux under nitrogen for five hours. The reaction mixture was cooled and the product purified by preparative HPLC, using 10% ethyl acetate in hexane as eluant, to afford 3-methyl-4-hydroxy-5-(2-propen-1-yl)-7-(2-thienoyl)benzofuran, compound 4. An analytical sample was obtained by recrystallization from ether/hexane. 1H NMR d 2.43 (3H, d, J=2 Hz), 3.54 (2H, d, J=6 Hz), 5.30 (2H, m), 5.86 (1H, s), 6.10 (1H, m), 7.16 (1H, dd, J=4 Hz, 4 Hz), 7.34 (1H, d, J=2 Hz), 7.50 (1H, s), 7.65 (1H, d, J=4 Hz), 7.72 (1H, d, J=4 Hz).

Provenance & Evidence