Lithium Hydroxide → HCID 67020984, compound

HRID 12912Notes

Reaction equation

HRID 12912 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:10]=1[C:11]([F:14])([F:13])[F:12])=[O:5])C.[Li+].[OH-]>CO.O>[CH:16]1([CH2:15][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)[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 670209131-cyclopropylmethyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 67020984HCID 67020984, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-cyclopropylmethyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (120 mg, 0.46 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 layers were concentrated in vacuo to give 1-cyclopropylmethyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (100 mg, 93%), 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 layers were concentrated in vacuo

Sources & evidence

ORD record
ord-b7f5194d744d48d4a0c4411e09c0c4d1
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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