Protection of alcohols as silyl ethers
Description: Alcohols can be converted into silyl ethers with trimethylsilyl chloride (TMSCl) or similar silyl groups such as t-butyldimethylsilyl chloride (TBDMSCl). This is a useful procedure for the protection of alcohols.
The rest of this page is available to MOC Members only.
To get access to this page, plus over 2500 quizzes, the Reaction Encyclopedia, Org 1 / Org 2 summary sheets, and flashcards, sign up here for only 30 cents/ day!
When a base is used as a catalyst in this reaction, does it first react with the protecting agent via SN2 mechanism or is it added during step 2 to cause deprotonation of the alcohol.
The pyridine is added to deprotonate the cyclohexanol
Might want to mention that the mechanism of silyl ether removal is caused by the very strong F-Si bond
Thank you, very good suggestion.