Sodium Hydroxide → 2-(5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid

HRID 2043746Notes

Reaction equation

HRID 2043746 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][C:8]([O:10]CC)=[O:9])[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[N:5]=[C:4]([C:13]([F:16])([F:14])[F:15])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66016896ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate

Product 1

HCID 660151092-(5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acidYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate (218 mg, 0.85 mmol) in tetrahydrofuran (1 mL) was treated with sodium hydroxide (0.2 mL, 50% aqueous solution) in water (0.6 mL), and stirred at ambient temperature for 4 h. The reaction mixture was then diluted with water (15 mL) and was concentrated under reduced pressure. The reaction mixture was acidified with concentrated hydrochloric acid to pH 1. The resulting mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated to give 140 mg of the title compound. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-86aa2f914b1f4cadb3dd5318c5c353b2
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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