A Convenient Procedure for Isolation of Alcohols After Cleavage of Protective Groups with Tetra-n-Butylammonium Fluoride

Abstract

Polar alcohols obtained from their β-(trimethylsilyl) ethoxymethyl (SEM) ethers by deprotection using the tetra-n-butylammonium fluoride reagent, can be efficiently isolated after quantitative removal of the excess reagent as the insoluble tetra-n-butylammonium perchlorate salt. Standard extractive workup then gives the alcohols in high yield. The method is applicable to any reaction involving the use of tetra-n-butylammonium fluoride for the removal of protective groups.