Morpholine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-morpholinoethoxy)phenyl)but-1-enyl)phenol
Reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21]Cl)=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:17][CH:18]=3)=[CH:7][C:5]=2[CH:6]=1Participants
4
Procedure
According to the same procedure as example 1, step E described, 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (70 mg, 1.0 eq, made by example 11, step D) was reacted with morpholine (1 mL) in MeOH (3 mL) under reflux to give the desired product (61 mg, 79%, Z/E=1/2) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.23 (s, 1H), 7.21 (d, J=8.4 Hz, 1H), 7.13 & 7.09 (d, J=8.6 Hz, 2H), 7.00 (d, J=8.4 Hz, 1H), 6.83 & 6.80 (d, J=8.6 Hz, 2H), 6.72 & 6.69 (d, J=8.6 Hz, 2H), 6.45 (s, 1H), 6.43 (d, J=8.8 Hz, 2H), 4.12 & 3.94 (t, J=5.6 Hz, 2H), 3.76 & 3.71 (t, J=4.8 Hz, 4H), 2.83 & 2.71 (t, J=5.6 Hz, 2H), 2.61 & 2.52 (t, J=4.4 Hz, 4H), 2.49 (q, J=7.2 Hz, 2H), 0.91 (t, J=7.2 Hz, 3H); m/z=504[M+1]+.