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Synthesis 1994; 1994(10): 1018-1020
DOI: 10.1055/s-1994-25626
short paper
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Facile Synthesis of 6-Hydroxyindole and 6-Methoxyindole via Regioselective Friedel-Crafts Acylation and Baeyer-Villiger Oxidation

Katsunori Teranishi* , Shin-ichi Nakatsuka, Toshio Goto
  • *Laboratory of Organic Chemistry, School of Agriculture, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
27 September 2002 (online)

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A facile synthesis of 6-hydroxyindole and 6-methoxyindole starting from indole is described. Regioselective chloroacetylation of 1-pivaloylindole followed by Baeyer-Villiger oxidation offers introduction of an oxygen function into the 6-position of the indole ring. Deacylation of 6-chloroacetyl-1-pivaloylindole gives 6-hydroxyindole which is converted to 6-methoxyindole by methylation. The overall yield of 6-hydroxyindole and 6-methoxyindole from indole is 54 and 37%, respectively.