Water → 3-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid

HRID 1191167

Reaction equation

HRID 1191167 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[O:5])C.O.[OH-].[Na+]>CO>[C:11]([C:9]1[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH3:15])[N:8]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 2799344ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 7205293-tert-butyl-1-methyl-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (1.08 g, 5.14 mmol, prepared as described in the previous step) was dissolved in MeOH (15 mL), and H2O (15 mL) and 2.5 M aqueous NaOH (5.00 mL, 12.5 mmol) was added. The resulting mixture was stirred at room temperature for 72 h, and then extracted with Et2O (2×10 mL). The aqueous layer was acidified to ca. pH 2 using 3 M aqueous HCl and extracted with DCM (3×20 mL). The combined organic extracts were dried over anhydrous MgSO4 and filtered, and the solvent was removed under reduced pressure to yield the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 6.80 (s, 1H), 4.15 (s, 3H), 1.32 (s, 9H).

Workup

  1. extractionextracted with Et2O (2×10 mL)
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c00ee2b444148c6b66385e89981b3f5
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Linked notes

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