Preparative Synthesis via Continuous Flow of 4,4,5,5-Tetramethyl-2-(3-trimethylsilyl-2-propynyl)-1,3,2-dioxaborolane: A General Propargylation Reagent
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- 作者：Daniel R. Fandrick ; Frank Roschangar ; Chunyoung Kim ; Byoung J. Hahm ; Myoung H. Cha ; Hyoun Y. Kim ; Gyesang Yoo ; Taeyun Kim ; Jonathan T. Reeves ; Jinhua J. Song ; Zhulin Tan ; Bo Qu ; Nizar Haddad ; Sherry Shen ; Nelu Grinberg ; Heewon Lee ; Nathan Yee ; Chris H. Senanayake
- 刊名：Organic Process Research & Development
- 出版年：2012
- 出版时间：May 18, 2012
- 年：2012
- 卷：16
- 期：5
- 页码：1131-1140
- 全文大小：1112K
- 年卷期：v.16,no.5(May 18, 2012)
- ISSN：1520-586X
文摘
A scalable process for the preparation of 4,4,5,5-tetramethyl-2-(3-trimethylsilyl-2-propynyl)-1,3,2-dioxaborolane from trimethylsilylpropyne, isopropyl pinacol borate, and n-butyllithium is described. Problems associated with implementing a typical aqueous workup and batch process into production due to borolane 鈥渁te鈥?equilibration and protonolysis are presented. To address these issues, a continuous-flow and distillation process was developed which efficiently produced 297 kg of the key propargylation reagent.