Lithium Hydroxide → 1-(2-methoxyethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid

HRID 12899Notes

Reaction equation

HRID 12899 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:15][CH2:16][O:17][CH3:18])[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[OH-].[Li+]>CO.O>[CH3:18][O:17][CH2:16][CH2:15][N:9]1[C:10]([C:11]([F:14])([F:12])[F:13])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67020970HCID 67020970, compound

Product 1

HCID 670208811-(2-methoxyethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acidYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(2-methoxyethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (0.291 g, 1.09 mmol) in methanol (3 mL) and water (3 mL) was added lithium hydroxide (0.072 g, 1.73 mmol). The reaction mixture was stirred at reflux for 2 h, and then the solution was concentrated under reduced pressure to remove the methanol. The residue was then acidified carefully with 6.0 N aqueous HCl. The resulting mixture was extracted with methylene chloride (3×25 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated in vacuo to provide 1-(2-methoxyethyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid as a orange oil (0.183 g, 71%), which was used without further purification. Mass spectrum: m/z: 239.0 (M+1).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationthe solution was concentrated under reduced pressure
  3. customto remove the methanol
  4. extractionThe resulting mixture was extracted with methylene chloride (3×25 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e3a697e8b2c408ea9d93fe69790edfd
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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