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 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
D J
DJ
Department of Chemistry, University of California, Irvine, California 92717-2025, USA.
Rychnovsky
S D
SD
D000107:Acetylation; D004952:Esters / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009942:Organometallic Compounds / Q000737:chemistry*; D013057:Spectrum Analysis
D004952:Esters; D004987:Ethers; D009942:Organometallic Compounds; C035719:diisobutylaluminum