Lithium Hydroxide → 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

HRID 1098572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098572
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]([O:11]CC)=[O:10])[C:6]([C:14]([F:17])([F:16])[F:15])=[N:5]1)([CH3:3])[CH3:2].[OH-].[Li+]>C(O)C.O.O1CCOCC1.O>[CH:1]([N:4]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[C:6]([C:14]([F:17])([F:16])[F:15])=[N:5]1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 57574507ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 667293411-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 69104347Dioxane ethanol waterLösungsmittel

Versuchsvorschrift

A solution of ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (266 mg, 1.06 mmol) and lithium hydroxide (102 mg, 4.25 mmol) in ethanol:water:dioxane (1:1:1, 6 mL) was warmed to 40° C. and stirred overnight. The mix cooled to RT, diluted with water (25 mL) and washed with ether (20 mL). The aqueous phase made acidic with 3N HCl (pH˜2) and extracted with ethyl acetate (2×15 mL). The combined ethyl acetate layers were washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to give 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (199 mg, 84% yield) as a white solid. MS (ESI) m/z: 223.0.

Aufarbeitung

  1. washwashed with ether (20 mL)
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washThe combined ethyl acetate layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-81b9401da93447fb8d398e6e4308b8d1
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143293B2

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