Potassium Hydroxide → 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetic acid

HRID 2359156Notes

Reaction equation

HRID 2359156 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([O:17][CH3:18])[C:13]([O:15]C)=[O:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[OH-].[K+]>CO>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([O:17][CH3:18])[C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58432030methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate

Product 1

HCID 584320232-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate (0.204 g, 0.83 mmol) in dry MeOH (5 mL) under argon was added a solution of KOH in MeOH (1.6 mL of a 0.5 M solution, 8.3 mmol) and the reaction was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and the volatiles were removed under reduced pressure. The residue was diluted with saturated aqueous NH4Cl and extracted with EtOAc. Additional EtOAc was then used to extract the aqueous phase as the pH was adjusted from ˜8 to ˜2 using concentrated HCl. The combined organics were dried over Na2SO4, filtered, and the solvents removed under reduced pressure to yield 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetic acid (0.18 g, 95%) which was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customthe volatiles were removed under reduced pressure
  4. additionThe residue was diluted with saturated aqueous NH4Cl
  5. extractionextracted with EtOAc
  6. extractionto extract the aqueous phase as the pH
  7. dry with materialThe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-b3bf478674094a0e80780e7c4fe71f33
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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