Sodium Hydroxide → 1-(4-tert-Butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

HRID 1748561Notes

Reaction equation

HRID 1748561 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:14][CH:13]=2)[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+]>CO>[C:22]([O:21][CH2:20][CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)=[CH:17][CH:16]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 897349361-(4-tert-butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 897352361-(4-tert-Butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acidYield 45.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-tert-butoxyethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (870 mg) in methanol (30 ml) was added 4 N aqueous solution of sodium hydroxide (10 ml), and stirred at room temperature overnight. After completion of the reaction, the organic solvent was evaporated in vacuo, then water and diethyl ether were added thereto, and the aqueous layer was separated. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the layer to pH 5, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (chloroform/methanol), isopropylether was added thereto, the precipitated solid was collected by filtration, and heat-dried at 60° C. in vacuo to give the titled compound (363 mg) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated in vacuo
  3. additionwater and diethyl ether were added
  4. customthe aqueous layer was separated
  5. additionTo the aqueous layer was added concentrated hydrochloric acid under ice-
  6. temperaturecooling
  7. extractionextracted with chloroform
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated in vacuo
  10. customThe obtained residue was purified with silica gel chromatography (chloroform/methanol), isopropylether
  11. additionwas added
  12. filtrationthe precipitated solid was collected by filtration
  13. customheat-dried at 60° C. in vacuo

Sources & evidence

ORD record
ord-dba437cd296a404b93817398099d942a
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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