4-Acetylbenzoic Acid → 4-[3-(5-benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-E-acryloyl]-benzoic acid

HRID 10620

Reaktionsgleichung

Reaktionsgleichung von HRID 10620
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[S:13]1[C:17]([C:18]2[C:19]([O:28][CH3:29])=[CH:20][C:21]([O:26][CH3:27])=[C:22]([CH:25]=2)[CH:23]=O)=[CH:16][C:15]2[CH:30]=[CH:31][CH:32]=[CH:33][C:14]1=2.[OH-].[Na+]>CN(C)C=O.O>[S:13]1[C:17]([C:18]2[C:19]([O:28][CH3:29])=[CH:20][C:21]([O:26][CH3:27])=[C:22](/[CH:23]=[CH:2]/[C:1]([C:4]3[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=3)=[O:3])[CH:25]=2)=[CH:16][C:15]2[CH:30]=[CH:31][CH:32]=[CH:33][C:14]1=2

Komponenten

6

Edukt 3

HCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 161159165-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

Produkt 1

HCID 99331504-[3-(5-benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-E-acryloyl]-benzoic acidAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-acetylbenzoic acid (1.50 g, 9.1 mmol) and 5-(benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde from Ex-3A (3.27 g, 11.0 mmol) in N,N-dimethylformamide (76 mL) was added a solution of sodium hydroxide (5 M, 7.3 mL, 36.5 mmol). The reaction mixture was allowed to stir at room temperature for 2 h and was then diluted with water to a volume of 150 mL. The solution was washed with dichloromethane and acidified with concentrated sulfuric acid to pH=3. The resulting solution was then extracted with dichloromethane. The dichloromethane extract was washed with brine, dried over sodium sulfate and concentrated. The resulting oily product solidified in ethanol. The solid was further stirred in ethanol for one day and collected by filtration. The solid was washed with ethanol, then dried in vacuo to afford the title compound as a yellow solid (2.2 g, 54%). 1H NMR (300 MHz, DMSO-d6) δ 8.36 (s, 1H), 8.21 (d, 2H), 8.07 (m, 3H), 7.93 (m, 3H), 7.82 (d, 1H), 7.32 (m, 2H), 6.86 (s, 1H), 4.08 (s, 3H), 4.00 (s, 3H). Anal. Calculated for C26H20O5S·1/6H2O: C, 69.78; H, 4.58; S, 7.17; found: C, 69.95; H, 4.69; S, 7.15. HPLC purity: 97.9% (area percentage).

Aufarbeitung

  1. washThe solution was washed with dichloromethane
  2. extractionThe resulting solution was then extracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. stirringThe solid was further stirred in ethanol for one day
  8. filtrationcollected by filtration
  9. washThe solid was washed with ethanol
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-80ec1d096bde430b80ffb02cef23687a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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