Water → 1-(2-chlorophenyl)-3-(methoxycarbonyl)-1H-pyrazole-5-carboxylic acid

HRID 877437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877437
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[O:14]C=CC=2)=[CH:11][C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:9]1.O.C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:29].[Na+]>C(#N)C.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([OH:14])=[O:29])=[CH:11][C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:9]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 23667635Sodium periodateHCID 43513895methyl 1-(2-chlorophenyl)-5-(furan-2-yl)-1H-pyrazole-3-carboxylate

Produkt 1

HCID 897828401-(2-chlorophenyl)-3-(methoxycarbonyl)-1H-pyrazole-5-carboxylic acidAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 61850Ruthenium trichlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred mixture of compound 6 (3.0 g, 9.9 mmol) in a mixture of acetonitrile (60 mL), water (80 mL) and carbon tetrachloride (60 mL) was added sodium periodate (8.3 g, 39 mmol) and ruthenium chloride (125 mg, 0.03 mmol) and the reaction mixture was stirred at room temperature for 72 h. On completion, solvent was removed, crude mass was dissolved in saturated sodium bicarbonate solution, extracted with ether (50 ml×3). Aqueous layer was acidified with 1N HCl and extracted with ethyl acetate (60 mL×4). The combined ethyl acetate layer was washed with brine, dried over sodium sulphate and concentrated to afford the title compound 7 (1.2 g, 44%) which was used for further reaction.

Aufarbeitung

  1. customOn completion, solvent was removed
  2. dissolutioncrude mass was dissolved in saturated sodium bicarbonate solution
  3. extractionextracted with ether (50 ml×3)
  4. extractionextracted with ethyl acetate (60 mL×4)
  5. washThe combined ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bb4fe09bf2744ca0b67aa3fc6d2d3437
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987318B2

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