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Establishment of salicylic acid derived silylation reagents for protection of alcohols
Results in Chemistry Pub Date : 2021-05-18 , DOI: 10.1016/j.rechem.2021.100139
Max Amann , Peter Fritz , Alexis Krupp , Stefan Heuser

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



中文翻译:

水杨酸衍生的硅烷化试剂的保护醇的建立

在这项工作中,我们描述了水杨酸衍生的2-[((三甲基甲硅烷基)氧基]-苯甲酸甲酯(TMSSME)及其TBDMS-(TBDMSSME)和TIPS-analogous(TIPSSME)作为新型硅烷化试剂,可从醇中制备甲硅烷基醚。使用TMSSME可以对多种脂肪族和芳香族醇进行甲硅烷基化,产率为55-97%。在温和的反应条件下,Dowex(50Wx8)有效地催化了该反应。但是,使用相应的TBDMS和TIPS试剂进行甲硅烷基化需要改进的反应条件,并且仅在伯醇上以高收率进行

更新日期:2021-05-18
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