SYNTHESIS OF HYDROLYTICALLY STABLE tert-BUTYLDIMETHYLSILYL ETHERS OF HYDROXYANTHRAQUINONES

Abstract

A series of hydrolytically stable hydroxyanthraquinone tert-butyldimethylsilyl ethers was synthesized by hydroxyl group silylation, under optimized reaction conditions. Tert-butyldimethylsilylchloride and N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide were each used as the silylating agent in two different silylating procedures. The products were studied by several chromatographic and spectroscopic techniques (TLC, GC, MS, IR, UV-Vis, ¹H NMR). Some helpful notifications for the advantageous use of each procedure, in regard to the requirements of the application field, were also made.

Key Words:

• Hydroxyanthraquinones
• tert-butyldimethylsilyl ethers
• N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide
• tert-butyldimethylsilylchloride
• tert-butyldimethylsilylation of hydroxyl groups