Sodium Hydroxide → HCID 64450941, compound

HRID 1893708Notes

Reaction equation

HRID 1893708 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:22]=[CH:21][C:8]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[C:12]([CH3:20])=[N:11]2)=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[C:12]([CH3:20])=[N:11]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66889435HCID 66889435, compound

Product 1

HCID 64450941HCID 64450941, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

According to Scheme 2, Step 1: A solution of NaOH 3 M (108 mmol, 35.8 mL) was added slowly, at 0° C., to a solution of ethyl 1-(4-methoxybenzyl)-3-methyl-1H-pyrazole-4-carboxylate (43 mmol, 11.8 g) in MeOH (108 mL) and the reaction mixture was heated at 50° C. for 2 hours. After evaporation of the solvent, the residue was partitioned between a NaOH 1M solution and Et2O. The organic layer was washed with a NaOH 1M solution. The aqueous layer was acidified to pH=1-2 with a HCl 1M solution and the aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4, was filtered and was concentrated under reduced pressure to yield 1-(4-methoxybenzyl)-3-methyl-1H-pyrazole-4-carboxylic acid (37.8 mmol, 9.30 g, 88%) as a beige solid. The crude product was used without any purification.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between a NaOH 1M solution and Et2O
  3. washThe organic layer was washed with a NaOH 1M solution
  4. extractionthe aqueous phase was extracted with DCM
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-853b01d4b8914597845c3f5726d593c4
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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