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| 1-(2-氰乙基)-2-氧代环戊基甲酸甲酯的选择性水解脱羧 | |
| 引用本文： | 赵广乐,于亮,闫喜龙,王东华,陈立功. 1-(2-氰乙基)-2-氧代环戊基甲酸甲酯的选择性水解脱羧[J]. 有机化学, 2009, 29(9): 1440-1444 |
| 作者姓名： | 赵广乐 于亮 闫喜龙 王东华 陈立功 |
| 作者单位： | 1. 天津大学化工学院,天津,300072 2. 天津大学药物科学与技术学院,天津,300072 |
| 基金项目： | 河南省杰出人才创新基金 |
| 摘 要： | 对1-(2-氰乙基)-2-氧代环戊基甲酸甲酯(4)的选择性水解脱羧反应进行了系统研究. 发现上述化合物在碱的催化作用下主要生成开环副产物2-(2-氰乙基)己二酸二甲酯及2-(2-氰乙基)己二酸; 由于氰基在酸性介质中也可发生水解, 因此对1-(2-氰乙基)-2-氧代环戊基甲酸甲酯在酸性情况下水解脱羧的反应条件进行了探索, 发现在4 mol•L－1盐酸介质中, 50 ℃下反应24 h, 以84.0%的收率得到目标产物3-(2-氧代环戊基)-丙腈. |
| 关 键 词： | 1-(2-氰乙基)-2-氧代环戊基甲酸甲酯 3-(2-氧代环戊基)-丙腈 水解 脱羧 |
| 收稿时间： | 2009-01-05 |
| 修稿时间： | 2009-03-04 |
Selective Hydrolysis and Decarboxylation of Methyl [1-(2-Cyanoethyl)-2-oxocyclopentyl]carboxylate |
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| Zhao Guangle,Yu Liang,Yan Xilong,Wang Donghua,Chen Ligong. Selective Hydrolysis and Decarboxylation of Methyl [1-(2-Cyanoethyl)-2-oxocyclopentyl]carboxylate[J]. Chinese Journal of Organic Chemistry, 2009, 29(9): 1440-1444 | |
| Authors: | Zhao Guangle Yu Liang Yan Xilong Wang Donghua Chen Ligong |
| Affiliation: | ( School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072) ( School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072) |
| Abstract: | Selective hydrolysis and decarboxylation of methyl [1-(2-cyanoethyl)-2-oxocyclopentyl]- carboxylate (4) were studied. The ring-opened byproducts, dimethyl-2-(2-cyanoethyl)adipate and 2-(2-cyanoethyl)adipic acid, were obtained primarily in an alkaline medium. While, in an acid medium, the hydrolysis and decarboxylation of 4 were studied since the cyano group could also be hydrolyzed. 3-(2-Oxocyclopentyl)propanenitrile was yielded in 84.0% at 50 ℃ after 24 h in the medium of 4 mol•L－1 HCl after optimization. |
| Keywords: | methyl [1-(2-cyanoethyl)-2-oxocyclopentyl]carboxylate 3-(2-oxocyclopentyl)propanenitrile hydrolysis decarboxylation |
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