大学化学 >> 2022, Vol. 37 >> Issue (5): 2110030.doi: 10.3866/PKU.DXHX202110030

所属专题： 第2届全国大学生化学实验创新设计竞赛

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7-硝基苯并噻吩-2-甲酸乙酯合成实验的优化与改进

李家柱(), 洪莹莹, 满英秀, 李英豪, 李庆忠, 何涛   

  • 收稿日期:2021-10-12 录用日期:2021-11-04 发布日期:2022-03-14
  • 通讯作者: 李家柱 E-mail:jiazhu82@ytu.edu.cn
  • 作者简介:李家柱, Email: jiazhu82@ytu.edu.cn
  • 基金资助:
    烟台大学教学改革研究项目(jyxm2021014)

Optimization and Improvement of "Synthesis of Ethyl 7-Nitrobenzothiophene-2-Carboxylate"

Jiazhu Li(), Yingying Hong, Yingxiu Man, Yinghao Li, Qingzhong Li, Tao He   

  • Received:2021-10-12 Accepted:2021-11-04 Published:2022-03-14
  • Contact: Jiazhu Li E-mail:jiazhu82@ytu.edu.cn

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摘要：

有机合成实验是化学专业学生重要单列实验课程，目前选用的有机合成实验项目多为单步骤合成操作，对学生多步合成的衔接、化合物的检测和鉴定等方面的训练存在不足。7-硝基苯并噻吩-2-甲酸乙酯的合成是本校应用化学专业学生有机合成实验课程中的一个综合训练项目，但存在耗时较长、产率不稳定，后处理难度较大及使用有毒试剂等问题。本项目旨在改进苯并噻吩环系的合成方法和步骤，降低试剂用量，提高产率，优化后处理过程，减少有毒物使用和三废排放，使之更符合教学实验和绿色化学要求；同时，改进后的实验增加了有机波谱分析内容，训练学生通过红外光谱、核磁共振氢谱及质谱等方式对目标化合物进行表征，更有利于学生综合素质的培养。

关键词: 有机合成, 多步合成, 绿色化学, 苯并噻吩

Abstract:

Organic Synthesis Experiment is an important independent experimental course for chemistry students. Current organic synthesis experiments are mostly single-step synthesis, which are insufficient for students' training on connection of multi-step syntheses, compound detection, and identification. Synthesis of ethyl 7-nitrobenzothiophene-2-carboxylate is a comprehensive project in the Organic Synthesis Experiment course for students majoring in applied chemistry at our school; however, it suffers from long reaction times, low yields, difficult work-up, and toxic reagents. This project aims to improve the synthesis methods and procedures of the benzothiophene ring system by reducing the amounts of reagents, increasing the yield, and optimizing the work-up processes. This improved experiment is more suitable as a teaching experiment. Organic spectroscopy was also added in the improved experiment so that students can learn how to characterize target compounds through infrared spectroscopy, nuclear magnetic resonance, and mass spectrometry, which will improve students' comprehension and quality of learning.

Key words: Organic synthesis, Multi-step synthesis, Green chemistry, Benzothiophene