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Practical generation of 3,5‐dimethoxybenzyllithium: application to the synthesis of 5‐substituted‐resorcinols
Author(s) -
Azzena Ugo,
Dettori Giovanna,
Idini Maria Vittoria,
Pisano Luisa,
Sechi Grazia
Publication year - 2003
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.531
Subject(s) - chemistry , epoxide , electrophile , tetrahydrofuran , halide , ether , organic chemistry , alkyl , resorcinol , naphthalene , lithium (medication) , catalysis , combinatorial chemistry , medicine , solvent , endocrinology
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.