Methylamine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(methylamino)ethoxy) phenyl)but-1-enyl)phenol

To a stirred solution of 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)-phenyl)but-1-enyl)phenol (220 mg, 1.0 eq) in 15 mL MeOH was added 5 mL CH3NH2 (aq) and heated at 85° C. for 48 h. The organic solvent was removed in vacuo, water was added to the residue and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (105 mg, 48%, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.14 & 7.08 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.4 Hz, 1H), 6.87 & 6.78 (d, J=8.8 Hz, 2H), 6.73 & 6.69 (d, J=8.8 Hz, 2H), 6.49 & 6.42 (d, J=8.6 Hz, 2H), 6.45 (s, 1H), 4.10 & 3.92 (t, J=5.0 Hz, 2H), 3.00 & 2.89 (t, J=5.0 Hz, 2H), 2.53 & 2.46 (s, 3H), 2.50 (q, J=7.6 Hz, 2H), 0.91 (t, J=7.6 Hz, 3H); m/z=448[M+1]+.