A two-step ball milling method synthesizes and purifies α,β-unsaturated esters

William C. Shearouse; Chelsea M. Korte; James Mack

doi:10.1039/C0GC00671H

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Green Chemistry

Issue 3, 2011

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A two-step ball milling method synthesizes and purifies α,β-unsaturated esters

William C. Shearouse,^a Chelsea M. Korte^a and James Mack*^a

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Department of Chemistry, University of Cincinnati, 301 Clifton Court, Cincinnati, USA
E-mail: james.mack@uc.edu

Green Chem., 2011,13, 598-601

DOI: 10.1039/C0GC00671H
Received 11 Oct 2010, Accepted 24 Nov 2010
First published online 04 Jan 2011

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Over the last decade, solvent-free methods have been gaining interest as replacements for traditional organic chemistry techniques. While solvent-free methods are well known for many processes, a simple, solvent-free purification procedure that supplements them does not exist. We report the solvent-free synthesis of α,β-unsaturated esters using a solvent-free Horner–Wadsworth–Emmons (HWE) reaction using high-speed ball milling (HSBM). We were able to perform the HWE reaction on a variety of aldehydes, and isolate their respective a,b-unsaturated esters in high yields, purities, and diastereoselectivities.

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