University Chemistry ›› 2016, Vol. 31 ›› Issue (8): 86-88.doi: 10.3866/PKU.DXHX201510008

• Chemistry Laboratory • Previous Articles     Next Articles

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)

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

MSC2000: 

  • O6