Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell

Org Lett. 2017 Apr 21;19(8):2050-2053. doi: 10.1021/acs.orglett.7b00641. Epub 2017 Apr 4.

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.

Publication types

  • Research Support, Non-U.S. Gov't