4-Acetylbenzoic Acid → 4-[3E-(4-Ethoxy-2-methoxy-5-thiophen-2-yl-phenyl)-acryloyl]-benzoic acid
Reaction equation
[CH2:1]([O:3][C:4]1[C:11]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:10][C:7]([CH:8]=O)=[C:6]([O:17][CH3:18])[CH:5]=1)[CH3:2].[C:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1)(=[O:21])[CH3:20]>>[CH2:1]([O:3][C:4]1[C:11]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:10][C:7](/[CH:8]=[CH:20]/[C:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[O:21])=[C:6]([O:17][CH3:18])[CH:5]=1)[CH3:2]Participants
3
Procedure
The title compound was prepared by condensing 4-ethoxy-2-methoxy-5-thiophen-2-yl-benzaldehyde (Ex-53A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 210–212° C., 76% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.31 (s, 1H), 8.23 (d, 2H, J=9.0 Hz), 8.06–8.11 (m, 3H), 7.92 (d, 1H, J=16.2 Hz), 7.71 (d, 1H, J=3.9 Hz), 7.52 (d, 1H, J=5.1 Hz), 7.13 (dd, 1H, J=5.1, 3.9 Hz), 6.82 (s, 1H), 4.33 (q, 2H, J=6.1 Hz), 3.99 (s, 3H), 1.48 (t, 3H, J=6.1 Hz). MS (ESI) m/z=409 ([M+H]+, 100%). Anal. Calcd. for C23H20O5S.½H2O: C, 66.17; H, 5.07; S, 7.68. Found: C, 65.88; H, 5.24; S, 7.36.
Sources & evidence
- ORD record
- ord-71986f3dc47b45d791832c7efeb6f0ef
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094801B2
Reaction notes
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