(1-(4-METHOXYPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-5-YL)METHANOL → 1-(4-Methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

HRID 610111Notes

Reaction equation

HRID 610111 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:7]=[C:6]([CH2:8][OH:9])[N:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:4]=1.I([O-])(=O)(=O)=[O:21].[Na+]>C(#N)C.O.[Ru](Cl)(Cl)Cl>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:7]=[C:6]([C:8]([OH:21])=[O:9])[N:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:4]=1

Participants

6

Reactant 2

HCID 11471256(1-(4-METHOXYPHENYL)-3-(TRIFLUOROMETHYL)-1H-PYRAZOL-5-YL)METHANOLHCID 23667635Sodium periodate

Product 1

HCID 111619581-(4-Methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidYield 90%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To the solution of 3-trifluoromethyl-5-hydroxymethyl-1 -(4-methoxyphenyl)-1H-pyrazole (4.4007 mmol, 1.198 g) in acetonitrile (20 mL) and water (20 mL) was added sodium periodate (1.977, 2.1 eq.) and several crystals of ruthenium(III) chloride at 0° C. This reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was filtered through Celite to remove white solid impurity and the filter cake washed with 1:1 acetonitrile: water. The filtrate was evaporated in vacuo and the residue was taken up in water. The aqueous was made acidic (pH 3) by the dropwise addition of conc. HCl at 0° C. then extracted with ethyl acetate (3×); the ethyl acetate extracts were washed with brine, dried (MgSO4), and evaporated to gave 1.13 g of pure product (90%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customto remove white solid impurity
  3. washthe filter cake washed with 1:1 acetonitrile
  4. customThe filtrate was evaporated in vacuo
  5. additionby the dropwise addition of conc. HCl at 0° C.
  6. extractionthen extracted with ethyl acetate (3×)
  7. washthe ethyl acetate extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-4b7e3f39631a4a3198ef325ae94fc6d0
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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