Lithium Hydroxide → HCID 58972822, compound

HRID 12915Notes

Reaction equation

HRID 12915 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[Li+].[OH-]>CO.O>[OH:17][CH2:16][C:15]([N:9]1[C:10]([C:11]([F:12])([F:13])[F:14])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1)([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 589728691-(2-hydroxy-1,1-dimethyl-ethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 58972822HCID 58972822, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(2-hydroxy-1,1-dimethyl-ethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (328 mg, 1.17 mmol) in methanol (5 mL) and water (5 mL) was added LiOH (34 mg, 1.4 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-(2-hydroxy-1,1-dimethyl-ethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (280 mg, 95%), 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-e223e57aa3bc46948cdcf3b0a4bc1443
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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