Chemical Properties
clear colorless to yellow fuming liquid
Physical properties
bp 60°C/7 mmHg; colorless oil, d 1.151 g cm?3.
Solubility: sol most organic solvents such as pentane, CH2Cl2,
etc.
Uses
tert-Butyldimethylsilyl trifluoromethanesulfonate is involved in the introduction of a bulky tert-butyl dimethylsilyl group onto a cis-bis(alkenyl)oxirane used in Cope rearrangement. It is associated with a thiolane and promotes the chalcogenide-Morita-Baylis-Hillman reaction. Further, it is used as a highly reactive silylating agent. In addition to this, it is used to prepare enol silyl ethers by reacting with ketones and lactones.
Uses
t-Butyldimethylsilyl Trifluoromethanesulfonate is used as a highly reactive silylating agent and Lewis acid capable of
converting primary, secondary, and tertiary alcohols1b to the
corresponding TBDMS ethers, and converting ketones and
lactones, into their enol silyl ethers; promoting conjugate
addition of alkynylzinc compounds and triphenylphosphine5 to
α,β-enones; activation of chromones in [4 + 2] cycloaddition
reactions;rearrangement of allylic tributylstannyl silyl ethers;
activation of pyridine rings toward Grignard reagents and transalkylation
of tertiary amine N-oxides;and transformation of
N-t-butoxycarbonyl groups into N-alkoxycarbonyl groups.
Uses
TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is a highly reactive silylating agent and lewis acid capable of converting primary, secondary and tertiary alcohols to their respectctive TBDMS. TrifluoroMethanesulfonic acid tert-butyldiMethylsilyl ester is also used to covert ketones and lactones into their enol silyl ethers.
Preparation
to 24 g (0.16 mol) of t-butyldimethylchlorosilane
at 23°C under argon is added 14 mL (0.16 mol) of
trifluoromethanesulfonic acid dropwise. The solution is heated
at 60°C for 10 h, at which time no further hydrogen chloride
evolves (removed through a bubbler). The resulting product is
distilled under reduced pressure: 34 g (80% yield) of TBDMS
triflate; bp 60°C/7 mmHg.
