Chemical Properties
clear colorless to yellowish liquid
Uses
Tris(trimethylsiloxy)ethylene has been used in:
- stereospecific synthesis of insecticide ajuqarin-IV
- microwave-assisted synthesis of 2-hydroxy-1-phenylethanone
Preparation
Tris(trimethylsilyloxy)ethylene is prepared from the bis(trimethylsilyl) derivative of glycolic acid by either forming the enolate with Lithium
Hexamethyldisilazide at -78 °C in THF and trapping with Chlorotrimethylsilane, or by the reaction with Trimethylsilyl
Trifluoromethanesulfonate and Triethylamine at rt (eq 1).
storage
Tris(trimethylsilyloxy)ethylene is readily hydrolyzed in protic solvents. It should be stored in a sealed container protected
from the atmosphere. Since the reaction of the reagent with carboxylic acid chlorides and aldehydes under Lewis acid catalysis in
the absence of solvent is highly exothermic, large-scale preparations may require regulation of the reaction temperature either by
external cooling or by controlled addition of the reactants.
