Sodium Hydroxide → 5-(Benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid

HRID 535009Notes

Reaction equation

HRID 535009 reaction equation
[CH2:1]([O:8][C:9]1[N:13]([CH3:14])[N:12]=[C:11]([C:15]([O:17]C)=[O:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][C:9]1[N:13]([CH3:14])[N:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66751233Methyl 5-(benzyloxy)-1-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 667513585-(Benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 5-(benzyloxy)-1-methyl-1H-pyrazole-3-carboxylate (15.8 g, 64.0 mmol) and 8 M sodium hydroxide solution (20 mL) in tetrahydrofuran (100 mL) and methanol (100 mL) was stirred at 40° C. for 4 h. Solvent was removed and 6 M hydrochloric acid solution added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain a solid (13.5 g, 91%).

Workup

  1. customSolvent was removed
  2. addition6 M hydrochloric acid solution added to the mixture
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61dc719933bb4fcc9234faf1688d55b4
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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