Cyclopentyl methyl ether as a new and alternative process solvent

Abstract

Cyclopentyl methyl ether (CPME) has become available in commercial quantities since November 2005 from Zeon Corporation with approval by the Toxic Substances Control Act (TSCA) and the European List of Notified Chemical Substances (ELINCS). A high boiling point (106 °C) and preferable characteristics such as low formation of peroxides, relative stability under acidic and basic conditions, formation of azeotropes with water coupled with a narrow explosion range render CPME an alternative to other ethereal solvents such as tetrahydrofuran (THF), 2-methyl tetrahydrofuran (2-MeTHF), dioxane (carcinogenic), and 1,2-dimethoxyethane (DME). Conventional drying is unnecessary for general organometallic reactions including Grignard reactions, enolate formation, Claisen condensation, general reductions, and Pd-based transformations. © 2007 American Chemical Society.