Acetyl chloride → Indole

HRID 483132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483132
C(CC1(CC)CCC(C=C)CC1=O)(OC)=O.[CH2:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25]N)[CH3:18].C(Cl)(C)=O>CO>[NH:25]1[C:20]2[C:19](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:18]1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 2733210(2-Ethylphenyl)hydrazineHCID 142014342-Carbomethoxymethyl-5-ethenyl-2-ethylcyclohexanone

Produkt 1

HCID 798IndoleAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The more polar ketone isomer of 2-carbomethoxymethyl-5-ethenyl-2-ethylcyclohexanone (5.084 g, 22.66 mmol) and the 2-ethylphenylhydrazine (3.086 g, 22.66 mmol) were heated at reflux in 97 ml of methanol under nitrogen for 48 hours. The reaction was then cooled to 0° C., treated with 45.32 mmol (3.56 g, 3.22 ml) of AcCl and refluxed an additional 45 minutes. Cooling, concentration and flash chromatography afforded 2.772 g (8.52 mmol, 38%) of indole as an orange oil. Rf =0.47 in 15% ethyl acetate/petroleum ether on TLC.

Aufarbeitung

  1. temperaturerefluxed an additional 45 minutes
  2. temperatureCooling
  3. concentrationconcentration and flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b6e21d77676643a9a84bb7d23940e5fa
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578398

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