Lithium hydroxide, monohydrate → 1-[(4-Methoxy)phenyl]-3-(ethoxycarbonyl)pyrazole-5-carboxylic acid

HRID 394800Notes

Reaction equation

HRID 394800 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:10]2)=[CH:5][CH:4]=1.O.[OH-].[Li+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 544294771-[(4-Methoxy)phenyl]-3-(ethoxycarbonyl)-5-(methoxycarbonyl)pyrazole

Product 1

HCID 544762241-[(4-Methoxy)phenyl]-3-(ethoxycarbonyl)pyrazole-5-carboxylic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution 1-[(4-methoxy)phenyl]-3-(ethoxycarbonyl)-5-(methoxycarbonyl)pyrazole (4.0 g, 13.2 mmol) in 40 mL of tetrahydrofuran and 20 mL of water was added an aqueous solution of lithium hydroxide monohydrate (0.55 g, 13.2 mmol). The reaction was allowed to stir at ambient temperature for 1 h. The tetrahydrofuran was removed in vacuo and the aqueous was extracted with ether to remove unreacted diester. The aqueous layer was acidified with HCl and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated to afford 3.2 g (84%) of the title compound, which was used without further purification. LRMS (ES−): 289.0 (M−H)−.

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. extractionthe aqueous was extracted with ether
  3. customto remove unreacted diester
  4. extractionextracted with ethyl acetate
  5. washThe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-85b1c8f74ca142a999a069776894d647
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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