Chemical Properties
clear colorless to light brown fuming liquid
Physical properties
85–86 °C/12 mmHg; d 1.169 g cm?3.
Uses
Triethylsilyl trifluoromethanesulfonate acts as a silylating agent. It is also useful as a Lewis acid catalyst. Further, it reacts with 1-diazo-3,3-dimethyl-butan-2-one to prepare 1-diazo-3,3-dimethyl-1-(triethylsilyl)-2-butanone.
Uses
Triethylsilyl Trifluoromethanesulfonate can be used as potent silylating agent and as Lewis acid catalyst. Triethylsilyl ethers are generally
more stable towards hydrolysis than are trimethylsilyl ethers, and
consequently the Et3Si moiety has gained increasing use as a protecting group for alcohols. However, since it is often difficult to
silylate sterically hindered hydroxyl groups using Et3SiCl, triethylsilyl perchlorate and triethylsilyl triflate (Et3SiOTf) were introduced to overcome this problem. Jefford has reported that condensation
reactions of 2-trimethylsiloxyfuran with aldehydes can be catalyzed by Et3SiOTf to give mainly the threo addition product
(eq 8).
Preparation
Triethylsilyl Trifluoromethanesulfonate can be prepared by reacting chlorotriethylsilane with trifluoromethanesulfonic acid followed by
distillation.
