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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 22
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Original Articles

Synthesis of Novel Poly(ethyleneglycol)-400 Ionic Liquid and Its Application in Morita–Baylis–Hillman Reaction

, , &
Pages 3289-3297 | Received 04 Aug 2009, Published online: 26 Jul 2011
 

Abstract

Novel Poly(ethyleneglycol)-400 ionic liquid containing imidazolium cations have been synthesized by the atom-efficient reaction of 1,2-dimethylimidazole with p-toluenesulfonate; the p-toluenesulfonate provides the anionic component of the resultant ionic liquid. It have been used for the first time as a new solvent for the Morita–Baylis–Hillman reaction under ambient conditions. A wide variety of aldehydes and active olefins participate very efficiently, resulting in good to excellent yields of products.

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the Xinzhou Teachers University Foundation ([2008] 79), the Higher School Science & Technology Development Project of Shanxi Province Education Department (No. 2010124), and the National Natural Science Foundation of China (No. 208020421B0211).

Notes

a All reactions were performed with aldehydes (5 mmol) and activated alkenes (10 mmol) in a mixture of IL-400 and water (v/v, 1:1, 10 ml) in the presence of appropriate catalyst DABCO (5 mmol) at ambient temperature.

b Refers to isolated, pure products after silica-gel chromatography.

c The reaction was performed with benzaldehyde (5 mmol) and acrylonitrile (10 mmol) in 5 ml of IL-400 in the presence of appropriate catalyst DABCO (2.5 mmol) at ambient temperature.

d The reaction was performed with benzaldehyde (5 mmol) and acrylonitrile (10 mmol) in 5 ml of IL-400 in the presence of appropriate catalyst DABCO (5 mmol) at ambient temperature.

a All reactions were performed with benzaldehyde (5 mmol) and acrylonitrile (10 mmol) in a mixture of IL-400 and water (v/v, 1:1, 10 ml) in the presence of appropriate catalyst DABCO (5 mmol) at ambient temperature.

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