(1-(4-Methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-YL)methanol → 1-(4-Methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

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%).

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

ORD record

ord-4b7e3f39631a4a3198ef325ae94fc6d0

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998424