Water → HCID 58542576, compound

HRID 1843103Notes

Reaction equation

HRID 1843103 reaction equation
[F:1][C:2]([C:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]([O:16]CC)=[O:15])[N:7]([CH3:19])[N:6]=1)([CH3:4])[CH3:3].[OH-].[K+].O>CO>[F:1][C:2]([C:5]1[C:9]([C:10]([F:11])([F:12])[F:13])=[C:8]([C:14]([OH:16])=[O:15])[N:7]([CH3:19])[N:6]=1)([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58542538HCID 58542538, compound

Product 1

HCID 58542576HCID 58542576, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 700 mg (2.48 mmol) of ethyl 3-(2-fluoropropan-2-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate in 10 ml of methanol is admixed with 208 mg (3.72 mmol) of potassium hydroxide and 1 ml of water and heated at 50° C. for one hour. The reaction mixture is concentrated by evaporation, admixed with water and extracted with diethyl ether. The aqueous phase is acidified with dilute hydrochloric acid and extracted twice with ethyl acetate, and the organic phase is dried over sodium sulphate and, after filtration, is concentrated by evaporation. This gives 498 mg of 3-(2-fluoropropan-2-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (79%).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with diethyl ether
  3. extractionextracted twice with ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. filtrationafter filtration
  6. concentrationis concentrated by evaporation

Sources & evidence

ORD record
ord-afc6e6b7a21541c7900325aaa65fa010
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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