Paper
Applications of Diethoxymethane as a Versatile Process Solvent and Unique Reagent in Organic Synthesis
Published Jan 4, 2001 · and Neil W. Boaz, B. Venepalli
Organic Process Research & Development
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Abstract
Diethoxymethane (DEM) has recently become available in commercial quantities. It has unique properties and is useful in a variety of applications in organic synthesis. It is low boiling (88 °C), azeotropes with water, and has a very low affinity for water. It is stable under basic conditions and as manufactured does not require drying for use as a solvent, even for organometallic reactions. DEM is useful as a process solvent especially for sodium hydride reactions, organolithium chemistry, copper-catalyzed conjugate additions, and phase-transfer reactions. As such, DEM is a potential replacement for tetrahydrofuran (THF), dichloromethane (CH2Cl2), glyme (1,2-dimethoxyethane), and methylal (1,1-dimethoxymethane). DEM is also useful as an ethoxymethylating agent, a formaldehyde equivalent, and a carbonylation substrate. Due to these unique properties and applications, DEM has exciting potential for widespread use both as a reagent and especially as a preferred solvent.
Diethoxymethane (DEM) offers unique properties and applications in organic synthesis, making it a potential replacement for traditional solvents and reagents in various reactions.
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