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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 alpha-acetoxy ethers in good to excellent yields. It was found that, under mild acidic conditions, many alpha-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.
Kopecky et al. (Fri,) studied this question.