大学化学 >> 2016, Vol. 31 >> Issue (8): 86-88.doi: 10.3866/PKU.DXHX201510008

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2,4-二甲基吡咯-3,5-二羧酸二乙酯的合成——推荐一个大学有机化学实验

汪剑波*(),宗乾收,沈锦锦,毕成,吴晨俊   

  • 发布日期:2016-08-31
  • 通讯作者: 汪剑波 E-mail:wjb4207@mail.ustc.edu.cn
  • 基金资助:
    浙江省自然科学基金项目(LQ15B060005);嘉兴学院教学改革项目(70115030)

Synthesis of Diethyl 2,4-dimethyl-pyrrole-3,5-dicarboxylate: Recommending a University Organic Chemistry Experiment

Jian-Bo WANG*(),Qian-Shou ZONG,Jin-Jin SHEN,Cheng BI,Chen-Jun WU   

  • Published:2016-08-31
  • Contact: Jian-Bo WANG E-mail:wjb4207@mail.ustc.edu.cn
  • Supported by:
    浙江省自然科学基金项目(LQ15B060005);嘉兴学院教学改革项目(70115030)

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摘要：

采用Knorr吡咯合成法，以乙酰乙酸乙酯和亚硝酸钠为原料，在醋酸和锌粉作用下采用“一锅法”得到2,4-二甲基吡咯-3,5-二羧酸二乙酯。本实验涉及到控温、回流、重结晶、熔点测定、红外光谱及核磁共振等实验操作和分析检测方法。该实验原料简单易得、产物收率高，结合波谱解析方法，可以培养和提高学生合成实验的能力，加强学生对杂环合成和波谱解析的理解与分析。

关键词: 乙酰乙酸乙酯, 吡咯, Knorr合成法, 一锅法

Abstract:

Using Knorr pyrrole synthesis, diethyl 2,4-dimethyl-pyrrole-3,5-dicarboxylate was synthesized via one-pot method with ethyl acetoacetate and sodium nitrite as starting materials in the presence of acetic acid and zinc powder. The experiment involves the experimental operation and analyses including temperature control, reflux, recrystallization, melting point, IR and NMR spectroscopies. The advantages of the experiment are simple raw materials and high product yield. The experiment is helpful for cultivating and improving the synthesis ability of students, as well as in-depth understanding of heterocyclic synthesis and spectral analysis.

Key words: Ethyl acetoacetate, Pyrrole, Knorr synthesis, One-pot method