Sodium hydride → 2-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione

HRID 14459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 14459
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[C:18]([O:19]C(=O)C(C)C)=[C:17]([F:25])[C:16]([F:26])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1>O1CCCC1.Cl>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:11](=[O:12])[CH:13]([CH3:18])[CH3:14])[C:11]([C:13]2[CH:14]=[CH:15][C:16]([F:26])=[C:17]([F:25])[C:18]=2[OH:19])=[O:12])=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 24758Sodium hydrideHCID 68703339Isobutyric acid 6-[2-(4-chlorophenyl)acetyl]-2,3-difluorophenyl ester

Produkt 1

HCID 686997002-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-4-methyl-pentane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Sodium hydride (1.5 g, 37.5 mmol, 60% dispersion in mineral oil, 4 eq.) is added portionwise to a stirred solution of isobutyric acid 6-[2-(4-chlorophenyl)acetyl]-2,3-difluorophenyl ester (3.16 g, 8.97 mmol) in tetrahydrofuran (60 ml) over 15 min. The mixture is heated in an oil bath at 80° C. for 4 h. The reaction is cooled to room temperature, diluted with 2M HCl solution and washed with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound as a brown oil. The product is used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction is cooled to room temperature
  2. washwashed with ethyl acetate
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-23a03a55e48c4fb1add8abb696fa5369
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732435B2

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