The Development of a General and Tunable Method for Ester to Ether Reduction

The development of methods to easily synthesize chemical structures is of great importance in the field of organic chemistry. Ether, a well-known functional group, may appear to be simple to synthesize by known methods. Unfortunately, this is not always the case, especially in considering the Williamson ether synthesis. This general coupling method between an alcohol and haloalkane will not work in cases were the alkyl group on the haloalkane is substituted and/or bulky. One solution is to use esters as the starting point to then be reduced to ethers since esters are easier to synthesize from an alcohol and carboxylic acid. While several methods for this transformation have been successful, there are still limitations that hinder any of them from being widely used across all types of ester substrates. Using previous research in the literature as a starting point, both aromatic and non-aromatic ester model systems were studied to find a general and tunable method to reduce esters to ethers utilizing a two-step process. To accomplish this, a variety of esters were synthesized, from which two model systems were chosen. The model system esters were reduced to an intermediate acetal using a trapping reagent, and then the acetal was reduced to an ether. A solvent screen was also employed for the first step of the reaction and it was monitored using ReactIR for completion of the ester reduction. Noteworthy results include shorter reaction times compared to the literature and the ability to reduce aromatic esters