大学化学 >> 2026, Vol. 41 >> Issue (5): 141-148.doi: 10.12461/PKU.DXHX202511156

所属专题： 第5届全国大学生化学实验创新设计大赛

专题 上一篇    

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

阳昊霖, 樊傲翔, 宋毅, 陈洋   

  1. 贵州大学药学院, 贵州 贵阳 550025
  • 收稿日期:2025-11-21 录用日期:2026-02-25 发布日期:2026-05-21
  • 通讯作者: 陈洋 E-mail:ychen1@gzu.edu.cn Yang Chen
  • 基金资助:
    贵州大学大学生创新创业训练计划项目(gzusc2024134)

Preparation of benzofuran-5-formaldehyde based on formylation conjugated dehydrogenation tandem strategy: a recommended comprehensive teaching experiment for basic organic synthesis

Haolin Yang, Aoxiang Fan, Yi Song, Yang Chen   

  1. School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025, Guizhou Province, China
  • Received:2025-11-21 Accepted:2026-02-25 Published:2026-05-21
  • Contact: Yang Chen E-mail:ychen1@gzu.edu.cn

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摘要： 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。

关键词: 苯并呋喃-5-甲醛, 甲酰化, 共轭脱氢, 串联策略, 综合教学实验

Abstract: This study innovatively designs a comprehensive teaching experiment for synthesizing benzofuran-5-carbaldehyde through a tandem strategy involving formylation and conjugated dehydrogenation. Applying the principle of integrating theory with practice, we conducted in-depth mechanistic analysis and systematic optimization of the experimental procedure. Using commercially available 2,3-dihydrobenzofuran as starting material, the target product was successfully obtained via sequential Vilsmeier-Haack formylation and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated dehydrogenation, achieving an overall yield exceeding 80%. Subsequent low-temperature crystallization enhanced the final product purity to over 95%. This comprehensive experiment features operational simplicity, cost-effective materials, controllable duration, and minimal safety risks, meeting the “High-level, Innovative and Challenging” requirements for undergraduate laboratory education while effectively cultivating students’ innovative thinking and research skills.

Key words: Benzofuran-5-formaldehyde, Formylation, Conjugated dehydrogenation, Tandem strategy, Comprehensive teaching experiment