1-ethoxycyclopropanol

Verwenden1-Ethoxycyclopropanol is used for homoenolate formation, ring expansion to β-lactams and pyrrolines via 1-aminocyclopropanols, to cyclobutanones via 1-vinylcyclopropanols, and to cyclopentanones via 1-trimethylsiloxy-1- vinylcyclopropanes.[1]

synthetischePreparative Methods of 1-ethoxycyclopropanol: acyloin-type reaction of ethyl 3-halopropionates with highly dispersed Sodium (or Lithium) in refluxing Et2O in the presence of Chlorotrimethylsilane provides 1-ethoxy-1- trimethylsiloxycyclopropane in high yields. Use of sonochemical activation simplifies the procedure. Then, simple methanolysis (MeOH, ClSiMe3) leads to the hemiacetal (eq 1).Cyclization of optically pure β-halo esters gives enantiomerically pure cyclopropanes at C-2 and a 1:1 diastereomeric mixture at C-1.