Selective cleavage of phenolic tert-butyldimethylsilyl ethers using simple organic nitrogen bases

Simple organic nitrogen bases, such as Et3N, pyridine, DBU, etc., were found to be convenient and useful reagents for deprotection of TBDMS groups on acidic hydroxyl groups. The efficiency of these bases has an apparent order: 1° amine > 2° amine > 3° amine and aliphatic base > aromatic base. In aqueous DMSO and at room temperature, phenolic TBDMS ethers were removed selectively in the presence of alcoholic TBDMS ethers. And catalytic base can make these reactions complete. This method is high-yielding, fast, clean, safe and cost-effective.