4-Acetylbenzoic Acid → 4-[3E-{4-Fluoro-3-(thiophen-2-yl)-phenyl}-acryloyl]-benzoic acid

HRID 10630

Reaktionsgleichung

Reaktionsgleichung von HRID 10630
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.[C:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1)(=[O:17])[CH3:16].[OH-].[Na+]>CN(C)C=O.O>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:16]/[C:15]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=2)=[O:17])=[CH:4][C:3]=1[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 167688744-Fluoro-3-(thiophen-2-yl)benzaldehyde

Produkt 1

HCID 210416224-[3E-{4-Fluoro-3-(thiophen-2-yl)-phenyl}-acryloyl]-benzoic acidAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Fluoro-3-thiophen-2-yl-benzaldehyde (1.0 g, 4.85 mmol, from Ex-20A) and 4-acetylbenzoic acid (0.80 g, 4.87 mmol) were dissolved in dimethylformamide (55 mL). Sodium hydroxide solution (5 N, 3.88 mL) was added in one portion, and the mixture was stirred at room temperature for 3 h. The reaction was diluted with water (100 mL) and washed with ethyl acetate (100 mL). The aqueous phase was acidified with conc. HCl and extracted with ethyl acetate (2×100 mL). The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from ethanol provided 0.90 g (53%) of the title compound as a solid, m.p. 242–244° C. 1H-NMR (300 MHz, d6-DMSO) δ 13.31 (bs, 1H), 8.32 (dd, 1H, J=8.2 and 2.0 Hz), 8.24 (d, 2H, J=8.2 Hz), 8.07 (d, 2H, J=7.9 Hz), 7.98 (d, 1H, J=16.1 Hz), 7.92 (m, 1H), 7.80 (d, 1H, J=16.1 Hz), 7.69–7.73 (m, 2H), 7.41 (dd, 1H, 10.8 and 9.2 Hz), 7.20 (m, 1H). MS m/z=352 ([M]+, 50%), 343 (100%). HRMS (EI) Calcd. for C20H13FO3S: 352.0569. Found: 352.0571.

Aufarbeitung

  1. washwashed with ethyl acetate (100 mL)
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2a580c9cc4a04d5ca1251353720da926
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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