Sodium Hydroxide → HCID 71770376, compound

HRID 626286Notes

Reaction equation

HRID 626286 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH:22]([F:24])[F:23])=[N:8][N:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5])C.[OH-].[Na+]>C(O)C>[C:18]([N:9]1[C:10]([C:11]([F:17])([F:16])[C:12]([F:13])([F:14])[F:15])=[C:6]([C:4]([OH:5])=[O:3])[C:7]([CH:22]([F:24])[F:23])=[N:8]1)([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71770248HCID 71770248, compound

Product 1

HCID 71770376HCID 71770376, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-tert-Butyl-3-difluoromethyl-5-pentafluoroethyl-4-pyrazolecarboxylic acid ethyl ester (2.0 g, 5.50 mmol) in ethanol (10 ml) was admixed gradually with an 8N aqueous sodium hydroxide solution (2.0 ml) and stirred at room temperature for 3 h. The solvent was removed by rotary evaporation; the residue was taken up in water (40 ml) and extracted with diethyl ether (20 ml). Acidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×30 ml). The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed by rotary evaporation. N-tert-Butyl-3-difluoromethyl-5-pentafluoroethyl-4-pyrazolecarboxylic acid (1.83 g, 5.44 mmol, 99%) was isolated as a yellow solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. extractionextracted with diethyl ether (20 ml)
  3. extractionAcidification to pH 1 with 6M HCl was followed by extraction with ethyl acetate (3×30 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-a119210f8b794afe84b8b956b5388826
Source dataset
uspto-grants-2016_04
Patent number
US09309202B2

Reaction notes

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