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

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

The Journal of organic chemistry (2000-05-18)
D J Kopecky, S D Rychnovsky
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 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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in hexanes
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Diisobutylaluminum hydride solution, 1.0 M in cyclohexane
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Diisobutylaluminum hydride solution, 1.0 M in toluene
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Sigma-Aldrich
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