Acetyl chloride → Indole

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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.

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