Facile synthesis of 6-hydroxyindole and 6-methoxyindole via regioselective Friedel-Crafts acylation and Baeyer-Villiger oxidation

Article abstract of DOI:10.1055/s-1994-25626

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.