An efficient and highly selective deprotecting method for β-(trimethylsilyl)ethoxymethyl ethers

Article abstract of DOI:10.1021/jo0107204

A series of β-(trimethylsilyl)ethoxymethyl ethers were hydrolyzed to their corresponding alcohols in high yields by using a catalytic amount of CBr₄ (15%) in MeOH under refluxing reaction conditions. The chemoselective deprotection between trialkylsilyl and β-(trimethylsilyl)-ethoxymethyl-protected alcohols can be achieved by using an alcohol with steric hindrance such as iPrOH. The selectivity also can be achieved in the CBr₄/MeOH reaction mixture under ultrasonic reaction conditions.