Lithium Hydroxide → HCID 58972819, compound

HRID 12919Notes

Reaction equation

HRID 12919 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH:15]2[CH2:18][CH2:17][CH2:16]2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[Li+].[OH-]>CO.O>[CH:15]1([N:9]2[C:10]([C:11]([F:12])([F:13])[F:14])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)[CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58972878HCID 58972878, compound

Product 1

HCID 58972819HCID 58972819, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-cyclobutyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (117 mg, 0.45 mmol) in methanol (5 mL) and water (5 mL) was added LiOH (13 mg, 0.54 mmol). The reaction mixture was stirred at reflux overnight, and then the solution was concentrated under reduced pressure to remove the methanol. The residue was diluted with water and the solution was acidified to pH=2 with concentrated HCl. The resulting mixture was then extracted with ethyl acetate three times. The combined organic extracts were concentrated in vacuo to give 1-cyclobutyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (93 mg, 89%), which was used without further purification.

Workup

  1. temperatureat reflux overnight
  2. concentrationthe solution was concentrated under reduced pressure
  3. customto remove the methanol
  4. additionThe residue was diluted with water
  5. extractionThe resulting mixture was then extracted with ethyl acetate three times
  6. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-1c112fd730ac41e6910cb80a87e5426e
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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