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■ 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

Abstract

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.