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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Study of the Room-Temperature Synthesis of Oxime Ethers by using a Super Base
Tomasz Kosmalski1, Renata Studzińska1, Natalia Daniszewska1
1Department of Organic Chemistry Faculty of Pharmacy Collegium Medicum Nicolaus Copernicus University Jurasza 2 85-067 Bydgoszcz Poland.
Abstract:
In this study, we present a convenient method for the synthesis of oxime ethers by reacting oximes with various chlorides (alkyl, functionalized alkyl, and benzyl) and with the subsequent use of a super base-pulverized potassium hydroxide in DMSO. The reactions take place at room temperature and the products are obtained in high yields. The final products were received within 2 min to 3 h. In addition, the compounds do not require chromatographic separation. The structure elucidation of the titled compounds was performed by using 1H NMR and 13C NMR spectroscopy as well as mass spectrometry. The presented method of synthesis for oxime ethers is environmentally friendly, because neither water cooling or heating of the reaction mixture/solvents (necessary for chromatographic purification) is required. The synthesis can be carried out very easily on a large scale.
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