Reaktion #481998

Reaktionsgleichung

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

carbon tetrachloride acetonitrile water

sodium periodate

→

title compound

Ausbeute 53.1%

1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-pyrazole-5-carboxylic acid

Ausbeute 53.1%

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a solution of 1-[(4-methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole (1.0 g, 2.63 mmol) in 4:4:6 carbon tetrachloride/acetonitrile/water was added sodium periodate (2.5 g, 11.8 mmol) and ruthenium (III) chloride monohydrate (11 mg, 0.05 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 0.5 g (53%) of the title compound as a solid. LRMS (ES−): 357.0 (M−H)−.

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