(1-ETHOXYCYCLOPROPOXY)TRIMETHYLSILANE

Chemical Properties

clear colorless liquid

Physical properties

bp 50–53 °C/22 mmHg.

Uses

(1-Ethoxycyclopropoxy)trimethylsilane was used in the preparation of N-(1′-alkoxy)cyclopropyl-2-haloanilines.

Uses

The 1-Ethoxy-1-(trimethylsilyloxy)cyclopropane can be used as preparation of 3-metallopropionates; metal homoenolate precursor; γ-hydroxy esters; cyclopentenones; 3-aminopropionates; cyclopropylamine formation; 1-aminocyclopropanecarboxylic acids and 1-aminocyclopropanephosphonic acids; β- and γ-amino acids.
The 1-Ethoxy-1-(trimethylsilyloxy)cyclopropane is widely used in various reactions. Cyclization of optically pure β-halo esters gives cyclopropanone acetals enantiomerically pure at C-2 and a 1:1 diastereomeric mixture at C-1.
Use of Cyclopropanone Hemiacetals. Heating cyclopropanone hemiacetal at 100°Cin an aqueous buffer provides the cyclopropanone hydrate. It also serves as a source of homoenolate radical species with a catalytic amount of AgNO3.

Preparation

For the synthesis of the parent and the 2-monoalkyl-substituted compounds, reduction of ethyl 3- chloropropionate with sodium–potassium alloy in the presence of chlorotrimethylsilane in ether. A recent modification using ultrasound irradiation is much more convenient and more widely applicable. Other substituted derivatives are prepared by cyclopropanation of alkyl silyl ketene acetals with the Furukawa reagent (diiodomethane/diethylzinc).