4-Acetylbenzoic Acid → 4-(3E-{2-Methoxy-4-[2-(2-methoxy-ethoxy)-ethoxy]-5-thiophen-2-yl-phenyl}-acryloyl)-benzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:8]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:7][C:4]=1[CH:5]=O.[C:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:8]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:7][C:4]=1/[CH:5]=[CH:25]/[C:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)=[O:26]Participants
3
Procedure
The title compound was prepared by condensing 2-methoxy-4-[2-(2-methoxy-ethoxy)-ethoxy]-5-thiophen-2-yl-benzaldehyde (Ex-49A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 174–175° C., 61% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.23 (d, 2H, J=8.1 Hz), 8.05–8.11 (m, 3H), 7.91 (d, 1H, J=15.3 Hz), 7.72 (d, 1H, J=2.7 Hz), 7.52 (d, 1H, J=4.2 Hz), 7.11–7.15 (m, 1H), 6.86 (s, 1H), 4.39 (t, 2H, J=3.9 Hz), 3.99 (s, 3H), 3.89 (t, 2H, J=3.9 Hz), 3.64 (t, 2H, J=3.9 Hz), 3.48 (t, 2H, J=3.9 Hz), 3.25 (s, 3H). MS (ESI) m/z=483 ([M+H]+, 100%). Anal. Calcd. for C26H26O7S: C, 64.71; H, 5.43; S, 6.64. Found: C, 64.43; H, 5.34; S, 6.54.
Sources & evidence
- ORD record
- ord-e909956e834c433c90c3f67ce454f373
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094801B2
Reaction notes
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