Butyryl chloride → 5-Butyryl-2-indolinone

HRID 24438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24438
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=[O:14].[C:15](Cl)(=[O:19])[CH2:16][CH2:17][CH3:18]>ClCCCl>[C:15]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[NH:5][C:6](=[O:14])[CH2:7]2)(=[O:19])[CH2:16][CH2:17][CH3:18]

Komponenten

5

Edukt 3

HCID 8855Butyryl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 235593785-Butyryl-2-indolinoneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 15 g of aluminum chloride suspended in 30 ml of 1,2-dichloroethane in an ice bath was added 7.5 g of 2-oxindole and then 12 g of butyryl chloride. The resulting suspension was stirred at 50° C. overnight. The mixture was poured into ice water and extracted 3 times with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate, and concentrated to dryness to give a brown solid. The solid was chromatographed on silica gel (50% ethyl acetate in hexane) to give 4.3 g (38%) of 5-butanoyl-2-oxindole as a yellow solid.

Aufarbeitung

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined ethyl acetate layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customto give a brown solid
  6. customThe solid was chromatographed on silica gel (50% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1844e3b429f046d29690848235c17f53
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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