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Synlett 2008(17): 2702-2704  
DOI: 10.1055/s-0028-1067255
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Systematic Study of a Solvent-Free Mechanochemically Induced Domino Oxa-Michael-Aldol Reaction in a Ball Mill

Emilie M. C. Gérard, Hülya Sahin, Arantxa Encinas, Stefan Bräse*
Institut für Organische Chemie, Universität Karlsruhe (TH), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6088581; e-Mail: braese@ioc.uka.de;
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Publication History

Received 2 July 2008
Publication Date:
01 October 2008 (online)

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Abstract

A systematical investigation of the parameters influencing on mechanical processing, ball milling, of organic reactants has been carried out. As model reactions, domino oxa-Michael-aldol reactions yielding tetrahydroxanthenones have been chosen.

Key words

solvent-free - ball mill - domino oxa-Michael-aldol reaction - tetrahydroxanthenone - dihydrobenzopyran

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All reactions were performed in a Ball Mill PM 100 Retsch with a fixed transmission ratio (1:2). In a typical experiment, salicylaldehyde (1 equiv), cyclohexenone (1 or 2 equiv), and DABCO (0.5 equiv) were ball milled over periods of 30 min with five-minute breaks between each. Afterwards, the vessel and the balls were rigorously washed with EtOAc. The combined organic phases were washed three times with H2O, dried over Na2SO4, filtered off, and reduced under vacuum. The residue was purified via silica gel column chromatography.