Lithium hydroxide, monohydrate → 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid

HRID 1753076Notes

Reaction equation

HRID 1753076 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:18])[CH2:8][N:9]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[N:10]1)C>O.C1COCC1>[F:17][C:14]([F:15])([F:16])[C:11]1[CH:12]=[CH:13][N:9]([CH2:8][C:7]([OH:18])=[O:6])[N:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 2064143HCID 2064143, compound

Product 1

HCID 20608832-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acidYield 19.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (127 mg, 3.03 mmol) in water (0.5 mL) was added to (3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid ethyl ester (250 mg, 1.125 mmol) in THF (5 mL). The mixture was stirred at room temperature for 5 hours then the reaction mixture volume was reduced to one third by evaporation in vacuo. The aqueous residue was acidified using aqueous HCl (2M) to pH=5. The resulting off white solid was filtered, collected and dried, washed with ether to afford the title compound as a white solid (42 mg, 19%).

Workup

  1. customthe reaction mixture volume was reduced to one third by evaporation in vacuo
  2. filtrationThe resulting off white solid was filtered
  3. customcollected
  4. customdried
  5. washwashed with ether

Sources & evidence

ORD record
ord-9d52e78fb76b4841946e366f86da170a
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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