Iodoethane → Ethyl 1-ethyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 374420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 374420
[F:1][C:2]([F:14])([F:13])[C:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][NH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH3:22].C(OCC)(=O)C>C(#N)C.O>[CH2:11]([O:10][C:8]([C:7]1[C:3]([C:2]([F:1])([F:13])[F:14])=[N:4][N:5]([CH2:21][CH3:22])[CH:6]=1)=[O:9])[CH3:12]

Komponenten

7

Edukt 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178469923HCID 178469923, Verbindung

Produkt 1

HCID 18996914Ethyl 1-ethyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Ethyl 3-trifluoromethylpyrazole-4-carboxylate (5 g), potassium carbonate (3.48 g) and ethyl iodide (2.3 ml) in acetonitrile were heated at reflux overnight. After cooling, ethyl acetate and water were added and the organic phase separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried (magnesium sulphate) and evaporated under reduced pressure to give a yellow oil which was purified by crystallisation in hexane to produce 4-ethoxycarbonyl-1-ethyl-3-trifluoromethylpyrazole as white crystals (3.65 g), 1H NMR (CDCl3) δ1.25(3H,t), 1.45(3H,t), 4.10(2H,q), 4.20(2H,q) 7.90(1H,s) ppm.

Aufarbeitung

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. customthe organic phase separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried (magnesium sulphate)
  6. customevaporated under reduced pressure
  7. customto give a yellow oil which
  8. customwas purified by crystallisation in hexane

Quellen und Nachweise

ORD-Eintrag
ord-cb7a01555c604140a97f58ce6354160e
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05480857

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