Sodium Hydroxide → 1-Tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid

HRID 1750340Notes

Reaction equation

HRID 1750340 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]([O:19]CC)=[O:18])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]([OH:19])=[O:18])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86721178ethyl 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 534225981-Tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound (18.67 g, 64.31 mmol) obtained in step 1 and 1N aqueous sodium hydroxide solution (70.0 mL, 70 mmol) in ethanol (180 mL) was stirred at 70° C. for 14 hr, and concentrated under reduced pressure. To the residue were added water and 1N hydrochloric acid, and the precipitate was collected by filtration to give 1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazole-4-carboxylic acid (16.87 g, 64.3 mmol, 100%) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue were added water and 1N hydrochloric acid
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-92fda040b137408a80144480eedc0fe0
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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