【求助】求LiI/pyridine水解甲酯成酸的机理
求LiI/pyridine水解甲酯成酸的机理
Procedure:
To a solution of compound A (38 g, 0.12 mol) in pyridine (250 mL) was added lithium iodide (38 g, 0.28 mmol), and the resulting solution was heated at reflux for 2 h. The reaction mixture was cooled to room temperature and the pyridine removed under vacuum. To the resulting gum was added 1 N HCl (100 mL), the resulting mixture was stirred for 15 min at rt and then filtered in vacuum. The solid was washed with 1 N HCl and Et2O, dried in vacuum to afford compound B (30.0 g, yield : 82.6%) as a white solid
compound A is a "methyl ester"
compound B is an acid.
LiI/pyridine水解甲酯成酸,是不是这样的条件很温和？不能水解别的酯（比如乙酯，丙酯）？
[ Last edited by jiajilong_76 on 2009-7-12 at 11:38 ]
返回小木虫查看更多
今日热帖
京公网安备 11010802022153号
自己顶一下
吡啶中回流2h，条件很剧烈啊，不知道这样的操作有什么意义
楼主，是什么文献啊
J. Med. Chem. 1995,38, 98-108
名字：Nonpeptidic Inhibitors of Human Leukocyte Elastase. 5. Design, Synthesis,
and X-ray Crystallography of a Series of Orally Active 5-Aminopyrimidin-6-one-ContaininTgr ifluoromethyl Ketones
作者：Chris A. Veale,*ti Peter R. Bernstein,' Craig Bryant,' Christopher Ceccarelli,t James R. Damewood, Jr. ,t Roger Earley,t Scott W. Feeney,? Bruce Gomes,P Ben J. Kosmider,? Gary B. Steelman,' Roy M. Thomas,+ Edward P. Vacek,' Joseph C. Williams,$ Donald J. Wolanin,' and Sheila Woolsont，
自己顶一下
这个是我们客户写的专利啊， 机理是这样的，碘化锂的碘进攻甲基，生成碘甲烷跑掉， 另一边的氧生成锂盐，加点酸就水解成酸了， 所以如果是乙酯就不一定能水解得掉了，呵呵