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Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell
Robert A Green1, Katherine E Jolley1, Azzam A M Al-Hadedi1
1Department of Chemistry, University of Southampton , Southampton, Hampshire SO17 1BJ, U.K.
Abstract:
Electrochemical deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct. The electrochemical method removes the need for chemical oxidants, and added electrolyte (BF4NEt4) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h-1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alcohol protecting groups.
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