1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole → 1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-pyrazole-5-carboxylic acid

HRID 394816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394816
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[O:15]C=CC=3)=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]([C:24]([F:27])([F:26])[F:25])=[N:10]2)=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C(#N)C.O.I([O-])(=O)(=O)=[O:38].[Na+]>O.[Ru](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([OH:15])=[O:38])=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]([C:24]([F:26])([F:25])[F:27])=[N:10]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 179399581-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazoleHCID 22592919water acetonitrile CCl4HCID 23667635Sodium periodate

Produkt 1

HCID 179399451-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-pyrazole-5-carboxylic acidAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6093376Ruthenium trichloride hydrateKatalysator

Versuchsvorschrift

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)−.

Aufarbeitung

  1. customThe resulting biphasic reaction
  2. customThe reaction was quenched with 10% aq HCl
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of Celite
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 1:1 hexanes/ethyl acetate
  9. extractionextracted with sat'd aq Na2CO3 (2 times)
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate extracts were washed with brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a7daa4949a304f8e97f8f1eda67a8549
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602895B2

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