Hydrochloric Acid → 3-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylic acid

HRID 2391119Notes

Reaction equation

HRID 2391119 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([O:9]CC)=[O:8])[N:4]([CH2:12][C:13]([F:16])([F:15])[F:14])[N:3]=1.[OH-].[Na+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[N:4]([CH2:12][C:13]([F:15])([F:14])[F:16])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57441025ethyl 3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 133384343-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylic acidYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazole-5-carboxylate (1.74 g, 7.36 mmol) in tetrahydrofuran (5.0 mL) was added 8N sodium hydroxide (4.6 mL), and the mixture was stirred at room temperature for 2 hr. 6N hydrochloric acid (6.0 mL) was added to the mixture (pH=3), and the aqueous layer was extracted three times with ethyl acetate/tetrahydrofuran. Combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was filtrated, and washed with ethyl acetate/hexane to give the title compound (1.28 g, 84%) as a white powder.

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate/tetrahydrofuran
  2. washCombined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. filtrationthe residue was filtrated
  7. washwashed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-7859b5e728d745f7a19ccce2cc1a1702
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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