Tris(trimethylsilyloxy)ethylene

clear colorless to yellowish liquid

Tris(trimethylsiloxy)ethylene has been used in:

• stereospecific synthesis of insecticide ajuqarin-IV
• microwave-assisted synthesis of 2-hydroxy-1-phenylethanone

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).

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.