Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers

An optimized protocol for the DIBALH reductive acetylation of acyclic ester s 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 c onditions, many alpha-acetoxy ethers can be further reduced to the correspo nding ethers. This net two-step ester deoxygenation is an attractive altern ative to the classical Williamson synthesis for certain ethers.