Réaction #481995

Équation de réaction

1-[(4-methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazole

carbon tetrachloride acetonitrile water

sodium periodate

3-(trifluoromethyl)-4-cyano-pyrazole-5-carboxylic acid

→

title compound

Rendement 102.6%

1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-1H-pyrazole 5-(2-furyl)pyrazole

Rendement 102.6%

Conditions de réaction

Traitement

1. 1
   AutreThe resulting biphasic reaction
2. 2
   AutreThe reaction was quenched with 10% aq HCl
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   LavageThe organics were washed with brine
5. 5
   Séchagedried (MgSO4)
6. 6
   Filtrationfiltered through a pad of Celite
7. 7
   Concentrationconcentrated
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 1:1 hexanes/ethyl acetate
9. 9
   Extractionextracted with sat'd aq Na2CO3 (2 times)
10. 10
    Extractionextracted with ethyl acetate
11. 11
    LavageThe ethyl acetate extracts were washed with brine
12. 12
    Séchagedried (MgSO4)
13. 13
    Concentrationconcentrated

Mode opératoire

1-(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-pyrazole-5-carboxylic acid. To a solution of 1-[(4-methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazole (0.68 g, 2.04 mmol) in 4:4:6 carbon tetrachloride/acetonitrile/water was added sodium periodate (1.96 g, 9.2 mmol) and ruthenium (III) chloride monohydrate (42 mg, 0.20 mmol). The resulting biphasic reaction was stirred vigorously at ambient temperature for 24 h. The reaction was quenched with 10% aq HCl and diluted with ethyl acetate. The organics were washed with brine, dried (MgSO4), filtered through a pad of Celite and concentrated. The residue was dissolved in 1:1 hexanes/ethyl acetate and extracted with sat'd aq Na2CO3 (2 times). The combined aqueous extracts were acidified and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated to afford 0.42 g (67%) of the title compound as a solid. LRMS (ES−): 310.0 (M−H)−.

Source