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Paper | Special issue | Vol 44, No. 1, 1997, pp.157-163
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S2
A New Synthesis of 1-Hydroxyindoles and Spectra of 1-Hydroxyindole

Toshiyuki Henmi, Takeshi Sakamoto, and Yasuo Kikugawa*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan


Partial reduction of 1-[2-(trimethylsilyl)ethoxy]-2-oxindole (3) with AlH(iso-Bu)2 (DIBAL) and subsequent removal of the protecting group with (n-Bu)4NF affords 1-hydroxyindole (1) in sufficiently pure form to produce reliable spectral data (nmr, ms, and uv) for the first time; this methodology is applicable to the synthesis of other 1-hydroxyindoles.