Potassium Hydroxide → 1-(3-Phenylpropyl)pyrazole-4-carboxylic acid

HRID 18118Notes

Reaction equation

HRID 18118 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[N:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CO>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[N:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21958678Ethyl 1-(3-phenylpropyl)pyrazole-4-carboxylate

Product 1

HCID 219586571-(3-Phenylpropyl)pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester was then dissolved in methanol (30 ml), and potassium hydroxide (1.5 g) added. The mixture was refluxed for 5 hours under nitrogen, then the solvent removed under reduced pressure. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and acidified to pH 1-2 with 6N hydrochloric acid, then extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and the solvent removed under reduced pressure, to give 1-(3-phenylpropyl)pyrazole-4-carboxylic acid.

Workup

  1. temperatureThe mixture was refluxed for 5 hours under nitrogen
  2. customthe solvent removed under reduced pressure
  3. customThe residue was partitioned between methylene chloride and water
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f538017448b54189af7f9949fd751833
Source dataset
uspto-grants-2010_06
Patent number
US07741331B2

Reaction notes

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