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

Cholesterol has been shown to be electrochemically oxidized at a carbon electrode to form cholesta-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.