25436-27-5Relevant articles and documents
Trimethylsilyl Esters as Novel Dual-Purpose Protecting Reagents
Chen, Jyun-Siao,Huang, Po-Hsun,Hsieh, Ya-Chi,Liu, Jen-Wei,Hsu, Hsiao-Lin,Zhang, Kai-Min,Wu, Ren-Tsung,Chang, Ting-Shuo,Liu, Yu-Hao,Wu, Hsin-Ru,Luo, Shun-Yuan
supporting information, p. 754 - 762 (2021/12/02)
Trimethylsilyl esters, AcOTMS, BzOTMS, TCAOTMS, etc., are inexpensive and chemically stable reagents that pose a negligible environmental hazard. Such compounds prove to serve as efficient dualpurpose reagents to respectively achieve acylation and trimethylsilylation of alcohols under acidic or basic conditions. Herein, a detailed study on protection of various substrates and new methodological investigations is described.
Dealkylation of esters via treatment with N-(trimethylsilyl) diethylamine and methyl iodide
Yamamoto, Yasushi,Shimizu, Hideaki,Hamada, Yoshitaka
, p. 119 - 122 (2007/10/03)
A method for the conversion of esters to carboxylic acids has been reported. Reaction of methyl o-methoxybenzoate with N-(trimethylsilyl)diethylamine and methyl iodide, followed by hydrolysis, afforded o-methoxybenzoic acid with a 94% yield based on 96% conversion. Methyl esters of not only aromatic acids but also aliphatic acids were converted to the corresponding acids with high yields. A combination of N-(trimethylsilyl)dimethylamine and methyl iodide was also effective to give p-methylbenzoic acid with a 85% yield based on 90% conversion from the corresponding methyl ester.
