Potassium Hydroxide → 155377-11-0

HRID 374419Notes

Reaction equation

HRID 374419 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([O:10]CC)=[O:9])[C:5]([C:13]([F:16])([F:15])[F:14])=[N:4]1)[CH3:2].[OH-].[K+]>C(O)C.O>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([C:13]([F:15])([F:14])[F:16])=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 18996914Ethyl 1-ethyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 18996921155377-11-0Yield 97.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1-ethyl-3-trifluoromethylpyrazole-4-carboxylate (2.17 g) was dissolved in ethanol and potassium hydroxide (1.06 g) in water was added. The reaction was stirred at room temperature overnight. Ethanol was removed under reduced pressure and the resulting residue partitioned between water and ether. The aqueous layer was separated, acidified with hydrochloric acid (2M) and extracted with ether. The combined organic extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo to give 1-ethyl-3-trifluoromethylpyrazole-4-carboxylic acid as a white solid (1.86 g). NMR (CDCl3) δ1.45(t,3H), 4.20(q,2H), 7.95(s,1H).

Workup

  1. customEthanol was removed under reduced pressure
  2. customthe resulting residue partitioned between water and ether
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-af4729e6010847c8ab096931b504e87a
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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