반응 #481998

반응 방정식

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

carbon tetrachloride acetonitrile water

sodium periodate

→

title compound

수율 53.1%

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

수율 53.1%

반응 조건

후처리

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

실험 절차

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)−.

출처