Establishment of salicylic acid derived silylation reagents for protection of alcohols

Abstract

In this work, we describe salicylic acid derived 2-[(trimethylsilyl)oxy]-benzoic acid methyl ester (TMSSME) and its TBDMS- (TBDMSSME) and TIPS-analogous (TIPSSME) as novel silylation reagents to furnish silyl ethers from alcohols. Silylation readily occurred in yields of 55–97% with TMSSME for a variety of aliphatic and aromatic alcohols. The reaction was effectively catalyzed by Dowex (50Wx8) under mild reaction conditions. Silylation with the corresponding TBDMS- and TIPS-reagents, however, required modified reaction conditions and only occurred on primary alcohols in good yields

Keywords

• Alcohols
• Heterogeneous catalysis
• Protecting groups
• Silyl ether
• Green chemistry