Acetyl chloride → Indole

HRID 483132

反応式

HRID 483132 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 798Indole収率 38%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b6e21d77676643a9a84bb7d23940e5fa
出典データセット
uspto-grants-1986_03
特許番号
US04578398

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