2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → Ethyl 2-methyl-4-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinate

HRID 890473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890473
[F:1][C:2]([F:19])([F:18])/[C:3](/O)=[CH:4]/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.[CH2:20]([O:22][C:23](=[O:28])/[CH:24]=[C:25](\[NH2:27])/[CH3:26])[CH3:21]>C(#N)C>[CH2:20]([O:22][C:23](=[O:28])[C:24]1[C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:27][C:25]=1[CH3:26])[CH3:21]

Komponenten

4

Edukt 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 178520887HCID 178520887, Verbindung

Produkt 1

HCID 86597779Ethyl 2-methyl-4-(trifluoromethyl)-6-(4-(trifluoromethyl)phenyl)nicotinateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To an acetonitrile (50 ml) solution of (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethyl-phenyl)-but-2-en-1-one (4.7 g, 17 mmol; D. Barrett, P. D. Bentley, T. R. Perrior, Synthetic Commun. 1996, 26, 3401–3406) was added ethyl-3-aminocrotonate (4.27 g, 33 mmol) under an argon atmosphere. The mixture was heated at reflux for 12 h. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, n-heptane/ethyl acetate) to yield 2.2 g (5.8 mmol, 35%) of the title compound as yellow crystals.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography (silica gel, n-heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7b2a2b51e622453b9cc629fa565e5ec8
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995263B2

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