tert-Butyldimethylsilyl Trifluoromethanesulfonate

[69739-34-0] C7H15F3O3SSi (MW 264.33) InChI = 1S/C7H15F3O3SSi/c1-6(2,3)15(4,5)13-14(11,12)7(8,9)10/h1-5H3 InChIKey = WLLIXJBWWFGEHT-UHFFFAOYSA-N (highly reactive silylating agent and Lewis acid capable of converting primary, secondary, and tertiary alcohols1b to the corresponding TBDMS ethers, and converting ketones2 and lactones2a,3 into their enol silyl ethers; promoting conjugate addition of alkynylzinc compounds4 and triphenylphosphine5 to α,β-enones; activation of chromones in [4 + 2] cycloaddition reactions;6 rearrangement of allylic tributylstannyl silyl ethers;7 activation of pyridine rings toward Grignard reagents8 and transalkylation of tertiary amine N-oxides;9 and transformation of N-tert-butoxycarbonyl groups into N-alkoxycarbonyl groups10) Alternate Name: TBDMS triflate. Physical Data: bp 60 °C/7 mmHg; colorless oil, d 1.151 g cm−3. Solubility: sol most organic solvents such as pentane, CH2Cl2, etc. Analysis of Reagent Purity: 1H NMR (CDCl3) δ 1.00 (s, 9H, tert-Bu), 0.45 (s, 6H, Me). Form Supplied in: liquid; widely available. Preparative Method: 1b 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. Handling, Storage, and Precautions: the material should be stored under argon at 0 °C. The compound has an unpleasant odor and reacts rapidly with water and other protic solvents.