Practical generation of 3,5-dimethoxybenzyllithium: application to the synthesis of 5-substituted-resorcinols

✍ Scribed by Ugo Azzena; Giovanna Dettori; Maria Vittoria Idini; Luisa Pisano; Grazia Sechi

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 107 KB
• Volume: 17
• Category: Article
• ISSN: 0268-2605
• DOI: 10.1002/aoc.531

✦ Synopsis

Abstract

Reductive lithiation of 3,5‐dimethoxybenzyl methyl ether was successfully performed with lithium wire and a catalytic amount of naphthalene in dry tetrahydrofuran at −15°C, leading to the quantitative generation of 3,5‐dimethoxybenzyllithium. This organometallic compound, which can be stored for at least 24 h, was trapped with a variety of different electrophiles, including, besides aldehydes, non‐functionalized and functionalized alkyl halides and an epoxide. Accordingly, it is a useful intermediate in the synthesis of 5‐substituted natural and non‐natural resorcinols. Copyright © 2003 John Wiley & Sons, Ltd.