Improved Procedure for the Reductive Acetylation of Acyclic Esters and a New Synthesis of Ethers
- 17 December 1999
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (1) , 191-198
- https://doi.org/10.1021/jo9914521
Abstract
An optimized protocol for the DIBALH reductive acetylation of acyclic esters and diesters is described. This reductive acetylation procedure allows a wide variety of esters to be converted into the corresponding α-acetoxy ethers in good to excellent yields. It was found that, under mild acidic conditions, many α-acetoxy ethers can be further reduced to the corresponding ethers. This net two-step ester deoxygenation is an attractive alternative to the classical Williamson synthesis for certain ethers.Keywords
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