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

HRID 512596Notes

Reaction equation

HRID 512596 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-cea78574a4974139b73d27e2d7eed476
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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