Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)

被引：7

作者：

Firouzabadi, H ^{[1
]}

Iranpoor, N ^{[1
]}

Shaterian, HR ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Shiraz 71454, Iran

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2000年 / 166卷

关键词：

silylation; protecting groups; TBDMS carboxylate; TIPS caiboxylate; solvent-free reaction; imidazole;

D O I：

10.1080/10426500008076532

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Various types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2 degrees, 3 degrees hydroxyl groups are observed.

引用

页码：71 / 81

页数：11

共 20 条

[1] REAGENTS AND SYNTHETIC METHODS .61. REACTION OF HINDERED TRIALKYSILYL ESTERS AND TRIALKYLSILYL ETHERS WITH TRIPHENYLPHOSPHINE DIBROMIDE - PREPARATION OF CARBOXYLIC-ACID BROMIDES AND ALKYL BROMIDES UNDER MILD NEUTRAL CONDITIONS [J].