4.4 Article

Electrosynthesis of cholesta-4,6-dien-3-one from cholesterol on a laboratory synthetic scale

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 1, Pages 129-132

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.10.106

Keywords

Electrosynthesis; Cholesta-4,6-dien-3-one; Flow-through cell; Column electrolysis

Funding

  1. Ministry of Education, Sports, Culture, Science, and Technology of Japan [17790617]
  2. Grants-in-Aid for Scientific Research [17790617] Funding Source: KAKEN

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Cholesterol has been shown to be electrochemically oxidized at a carbon electrode to form cliolesta-4,6-dien-3-one in acetonitrile [Hosokawa, Y. Y.; Hakamata, H.: Murakami, T.; Aoyagi, S.; Kuroda, M.; Mimaki, Y.; Itoh, A.: Morosawa, S.; Kusu, F. Electrochim. Acta. 2009, 54, 6412-6416]. To further expand on this reaction in the field of organic synthesis, the electrolysis conditions of cholesterol were optimized on a laboratory synthetic scale. Using a flow-through column electrolysis system, cholesta-4,6-dien-3-one was efficiently produced at the applied potential of 1.9 V versus Ag/AgCl with a flow rate of 2.5 mL/min, providing a green tool for the synthesis of cholesta-4,6-dien-3-one. (C) 2009 Elsevier Ltd. All rights reserved.

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