Water → methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate

HRID 2359155Notes

Reaction equation

HRID 2359155 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([O:16][CH3:17])[C:13]([O-:15])=[O:14])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[K+].S(=O)(=O)(O)O.O.[C:25]([O-])(O)=O.[Na+]>CO>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([O:16][CH3:17])[C:13]([O:15][CH3:25])=[O:14])=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67388986potassium 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate

Product 1

HCID 58432030methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetateYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of potassium 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate (˜7.55 mmol) in dry MeOH under argon was added sulfuric acid (2.0 mL) dropwise. The mixture was heated at 80° C. for 17 hours. After cooling to room temperature, water was added then the mixture made basic with saturated aqueous NaHCO3 addition. The aqueous phase was extracted with EtOAc and the combined organics were washed with water and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (20-35% EtOAc-hexanes) provided methyl 2-(4-(1H-pyrazol-1-yl)phenyl)-2-methoxyacetate as a colorless oil (0.88 g, 47% yield for two steps).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organics were washed with water and brine
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (20-35% EtOAc-hexanes)

Sources & evidence

ORD record
ord-ab24011420d74a65aeffa37b63a69cfc
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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