Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate → Ethyl 1-(3-cyano-4-fluorophenyl)-5-(2-furyl)pyrazole-3-carboxylate
Reaktionsgleichung
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8](=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[Sn](Cl)(Cl)(Cl)Cl.[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][C:23]=1[C:30]#[N:31]>C(O)(=O)C>[C:30]([C:23]1[CH:24]=[C:25]([N:28]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:29]2)[CH:26]=[CH:27][C:22]=1[F:21])#[N:31]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To ethyl 4-(2-furyl)-2,4-dioxobutyrate (3.5 g, 16.7 mmol) in 50 mL of glacial acetic acid was added 4-fluoro-3-cyanophenylhydrazine tin chloride (6.3 g, 16.7 mmol). The reaction was stirred at 100° C. for 4 h. The reaction was allowed to cool to room temperature and the acetic acid was removed in vacuo. The residue was diluted with ethyl acetate and the organics were washed with saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was purified by recrystallization from hexane/ethyl acetate to afford 2.5 g (46%) of the title compound. LRMS (ES+): 326.1 (M+H)+.
Aufarbeitung
- temperatureto cool to room temperature
- customthe acetic acid was removed in vacuo
- additionThe residue was diluted with ethyl acetate
- washthe organics were washed with saturated aq NaHCO3 and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was purified by recrystallization from hexane/ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-3b797fd9114943efa69b30e57978a86f
- Quelldatensatz
- uspto-grants-2005_10
- Patentnummer
- US06958356B2
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