Lithium Hydroxide → 1-tert-Butyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 12864

Reaktionsgleichung

Reaktionsgleichung von HRID 12864
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[OH-].[Li+]>CO.O>[C:15]([N:9]1[C:10]([C:11]([F:13])([F:14])[F:12])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 2782985Ethyl 1-(tert-butyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 14820391-tert-Butyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirred mixture of 1-tert-butyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (3.000 g; 11.4 mmol) in methanol/water (1:1 ratio, 50 mL) was added lithium hydroxide (0.383 g; 16.0 mmol) at room temperature. The mixture was heated to reflux for 2 hr, then allowed to cool to room temperature and concentrated to approximately half of the original volume. The resulting mixture was acidified with 1N HCl to ˜pH 1 and extracted with methylene chloride. The extracts were dried over sodium sulfate, filtered and concentrated to provide 1-tert-butyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (2.47 g, 92%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hr
  3. concentrationconcentrated to approximately half of the original volume
  4. extractionextracted with methylene chloride
  5. dry with materialThe extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-74bbc7229e774ccda91f8e7165057b08
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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