3-Chloro-1-(2,3-dihydrobenzofuran-5-yl)propan-1-one → HCID 78135063, compound

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Reaction Steps

According to general procedure of McMurry reaction as example 1, step D described, 3-chloro-1-(2,3-dihydrobenzofuran-5-yl)propan-1-one (0.85 g, 1.0 eq) was reacted with (4-hydroxyphenyl)(4-(2-(methylamino)ethoxy)phenyl)methanone (1.0 g, 1.0 eq) to give 1.2 g desired product (85%, Z/E=1/1). 1H NMR (400 MHz, DMSO-d6) δ 9.87 (s, 1H), 7.02-7.54 (m, 6H), 6.70-6.84 (m, 5H), 4.22 (t, J=8.4 Hz, 2H), 4.03 (t, J=6.0 Hz, 2H), 3.48 (t, J=5.6 Hz, 2H), 2.89-3.05 (m, 4H), 2.42 (s, 3H), 2.13 (t, J=8.4 Hz, 2H); m/z=450[M+1]+.

Provenance & Evidence