1-(Thiophen-3-yl)propan-1-one → 4-(1-(4-(2-Chloroethoxy)phenyl)-2-(thiophen-3-yl)but-1-enyl)phenol

Participants

Reaction Steps

Following general procedure of McMurry reaction as described in example 1, step B, 1-(thiophen-3-yl)propan-1-one (0.5 g, 1.0 eq) was reacted with (4-(2-chloroethoxy)phenyl)(4-hydroxyphenyl)methanone (1.5 g, 1.5 eq) to give 1.3 g desired product (95% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.10-7.14 (m, 1H), 7.02-7.09 (m, 2H), 6.76-6.92 (m, 5H), 6.68-6.71 (m, 1H), 6.60-6.66 (m, 1H), 6.55-6.59 (m, 1H), 4.62 (s, 1H), 4.49 (s, 1H), 4.24 (t, J=6.0 Hz, 1H), 4.14 (t, J=6.0 Hz, 1H), 3.82 (t, J=6.0 Hz, 1H), 3.76 (t, J=6.0 Hz, 1H), 2.43-2.49 (m, 2H), 0.98 (t, J=7.6 Hz, 3H).

Provenance & Evidence