Indole → 1H-Indole-1-acetonitrile

HRID 8120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 8120
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]#[N:15]>CN(C)C=O.C(OCC)(=O)C>[N:1]1([CH2:13][C:14]#[N:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

6

Edukt 3

HCID 798IndoleHCID 11534BromoacetonitrileHCID 24758Sodium hydride

Produkt 1

HCID 122309041H-Indole-1-acetonitrileAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 0° C. solution of indole (7 g, 59.8 mmol) in 200 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 3.1 g, 77.7 mmol). After 20 minutes, bromoacetonitrile (4.2 ml, 59.8 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir overnight. The reaction mixture is diluted with ethyl acetate (500 ml) and washed with H2O (3×200 ml). The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 5% then 20% ethyl acetate in hexanes) to give 2.53 g of indol-1-yl-acetonitrile (27%).

Aufarbeitung

  1. washwashed with H2O (3×200 ml)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue is purified by flash chromatography (SiO2

Quellen und Nachweise

ORD-Eintrag
ord-7a4c2b57e5d34d249997ab15f038576e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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