Water → HCID 59638316, Verbindung

HRID 1037505

Reaktionsgleichung

Reaktionsgleichung von HRID 1037505
[OH:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.[Cl-].[Cl-].[Cl-].[Al+3].O.Cl[C:23]([CH3:26])([CH3:25])[CH3:24]>>[C:23]([C:8]1[CH:7]=[CH:6][C:5]2[N:4]([CH2:3][CH2:2][OH:1])[C:16]3[C:11]([C:10]=2[CH:9]=1)=[CH:12][C:13]([C:10]([CH3:11])([CH3:5])[CH3:9])=[CH:14][CH:15]=3)([CH3:26])([CH3:25])[CH3:24]

Komponenten

5

Edukt 4

HCID 962WaterHCID 10486tert-BUTYL CHLORIDEHCID 228287Carbazole-9-ethanol2×HCID 6451240Aluminum(III) Chloride2×

Produkt 1

HCID 59638316HCID 59638316, VerbindungAusbeute 84 %

Versuchsvorschrift

To a solution of 9-(2-hydroxy ethyl)carbazole (1.65 g, 7.81 mmol) in 2-chloro-2-methylpropane (25.0 ml) was added aluminum trichloride (0.54 g, 4.05 mmol) at room temperature under nitrogen atmosphere and stirring. After 1 minute, the addition of AlCl3, insoluble 9-(2-hydroxyethyl)carbazole disappeared. The reaction was carried out at room temperature for 25 minutes, and water (20.0 ml) was added. The product was extracted with ethyl acetate (3×20.0 ml). The organic layer was washed with water (3×60.0 ml), and then ethyl acetate was evaporated under vacuum. The product was applied to a silica gel column [ethyl acetate/hexanes (3.5:6.5)] to yield 2.1 g (84.0%) of a white solid after recrystallization from dichloromethane/hexanes.

Aufarbeitung

  1. waitThe reaction was carried out at room temperature for 25 minutes
  2. extractionThe product was extracted with ethyl acetate (3×20.0 ml)
  3. washThe organic layer was washed with water (3×60.0 ml)
  4. customethyl acetate was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-cbacbd3f2ddb4d4cbfce35d7438bda9d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546505B2

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