Sodium Hydroxide → 1-(2-Fluoroethyl)-1H-pyrazole-3-carboxylic acid

HRID 244671Notes

Reaction equation

HRID 244671 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([O:11]CC)=[O:10])=[N:5]1.[OH-].[Na+]>CO>[F:1][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[N:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58356400HCID 58356400, compound

Product 1

HCID 583563741-(2-Fluoroethyl)-1H-pyrazole-3-carboxylic acidYield 18.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl 1-(2-fluoroethyl)-1H-pyrazole-3-carboxylate (0.1 g) in methanol (5 ml) was added 2M sodium hydroxide (5 ml) and the mixture stirred at 20° C. for 18 h. The solvent was removed in vacuo and the residue dissolved in water (20 ml) and acidified to pH=4 using 2M hydrochloric acid then extracted with ethyl acetate (20 ml), dried over sodium sulphate and evaporated to give the title compound (16 mg) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water (20 ml)
  3. extractionthen extracted with ethyl acetate (20 ml)
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-bf56f6507401450891ed892050d630c0
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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