Sodium Hydroxide → 1-(2-Methoxyethyl)-1H-Pyrazole-5-Carboxylic Acid

HRID 2100362Notes

Reaction equation

HRID 2100362 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=[N:6]1.[OH-].[Na+]>C(O)C.O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=[N:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57799147HCID 57799147, compound

Product 1

HCID 252476851-(2-Methoxyethyl)-1H-Pyrazole-5-Carboxylic AcidYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 1-(2-methoxyethyl)-1H-pyrazole-5-carboxylate (Preparation 28, 710 mg, 3.6 mmol) was dissolved in ethanol (10 ml), a solution of sodium hydroxide (160 mg, 4.0 mmol) in water (5 ml) was added and the solution was stirred at room temperature for 2 hours. The ethanol was removed in vacuo and the residue was acidified with 2M HCl (approximately 2 ml) and extracted with dichloromethane (40 ml). The organic layers were dried over anhydrous Na2SO4, filtered and the dichloromethane removed in vacuo to give 590 mg of a pale yellow foam.

Workup

  1. customThe ethanol was removed in vacuo
  2. extractionextracted with dichloromethane (40 ml)
  3. dry with materialThe organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customthe dichloromethane removed in vacuo

Sources & evidence

ORD record
ord-815d031f92a5408d8a88ea8c5d674dc0
Source dataset
uspto-grants-2009_08
Patent number
US07572797B2

Reaction notes

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