Citation: Haolin Yang, Aoxiang Fan, Yi Song, Yang Chen. 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验[J]. University Chemistry, ;2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156 shu

基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验

School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025, Guizhou Province, China

Corresponding author: Yang Chen, ychen1@gzu.edu.cn
Received Date: 21 November 2025
Revised Date: 25 February 2026

本文创新性地设计了基于甲酰化-共轭脱氢的串联策略合成苯并呋喃-5-甲醛的综合实验。运用理论联系实际的思想，对反应机理进行了深度分析，对实验实施进行了系统性探究与优化。本新创实验以商品购买的2,3-二氢苯并呋喃作为起始原料，经过Vilsmeier-Haack甲酰化和2,3-二氯-5,6-二氰对苯醌(DDQ)共轭脱氢两步连续反应，顺利制得目标产物——苯并呋喃-5-甲醛，总收率可达80%以上。实验后期，低温析晶法有效提升了终产物的纯度，可达95%以上。本综合性教学实验具有操作简便可控、物料廉价易得、教学时长可控、安全风险度低等优点，满足本科实验教学“两性一度”需求，具有较好教学可行性，有益于培养学生的创新思维和探索精神。
- Benzofuran-5-formaldehyde,
- Formylation,
- Conjugated dehydrogenation,
- Tandem strategy,
- Comprehensive teaching experiment
1. [1]
2. [2]
3. [3]
4. [4]
  Z. Sun, J. Cheng, C. Xu, X. Zhang, Q. Zang, X. Yang, Y. He, A. Su, X. Peng, J. Chen. J. Med. Chem. 2025, 68, 3048.
5. [5]
  C.M. Phiri, A. Saxena, AIP Conf. Proc. 2023, 2535, 040007.
6. [6]
7. [7]
  A.Y. Lyapunov, D.A. Lega, V.G. Makhankova, L.S. Muravska, O.M. Vitsenko, D.M. Volochnyuk, S.V. Ryabukhin, J. Chem. Educ. 2025, 102, 803.
8. [8]
9. [9]
  M. Saitoh, J. Kunitomo, E. Kimura, H. Iwashita, Y. Uno, T. Onishi, N. Uchiyama, T. Kawamoto, T. Tanaka, C.D. Mol, et al., J. Med. Chem. 2009, 52, 6270.
10. [10]
  D.C. Cole, M. Asselin, D.H. Boschelli, A. Wissner, Y.D. Wang, A.S. Prashad, R. Dushin. Preparation of cyanopyridines as protein kinase inhibitors: USA, US20070287738[P], 2007-12-13.
11. [11]
  L.V. Sayson, R.J.P. Custodio, D.M. Ortiz, H.J. Lee, M. Kim, Y. Jeong, Y.S. Lee, H.J. Kim, J.H. Cheong, Eur. J. Pharmacol. 2020, 885, 173527.
12. [12]
  W.A.L. van Otterlo, G.L. Morgans, L.G. Madeley, S. Kuzvidza, S.S. Moleele, N. Thornton, C.B. de Koning, Tetrahedron 2005, 61, 7746.
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