Lithium Hydroxide → 1-Benzyl-1H-pyrazole-4-carboxylic acid

HRID 64301Notes

Reaction equation

HRID 64301 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 15237993ethyl 1-benzyl-1H-pyrazole-4-carboxylate

Product 1

HCID 64838761-Benzyl-1H-pyrazole-4-carboxylic acidYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 1-benzyl-1H-pyrazole-4-carboxylate (53.0 g, 0.23 mol) and LiOH (19.4 g, 0.46 mol) in THF (100 mL) and H2O (100 mL) was stirred at refluxed for 6 h. Then, THF was removed, the residue was acidify by 6 N HCl, precipitation was formed, filtered and dried to give the desired compound as a white solid (44.0 g, 92.8%). 1H NMR (DMSO-d6) δ 12.36 (s, 1H), 8.39 (s, 1H), 7.85 (s, 1H), 7.38-7.27 (m, 5H), 5.37 (s, 2H). MS (ESI) m/e [M+1]+ 202.9.

Workup

  1. temperatureat refluxed for 6 h
  2. customThen, THF was removed
  3. customprecipitation
  4. customwas formed
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-efda182c988940bfa68eb4005b892e58
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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