文章摘要
荆华青,李红亮.“一锅三步法”合成苯基-2-吡啶基甲醇[J].精细化工,2020,37(8):
“一锅三步法”合成苯基-2-吡啶基甲醇
Synthesis of phenyl-2-pyridyl methanol by “one-pot three-steps” method
投稿时间:2020-03-23  修订日期:2020-04-28
DOI:
中文关键词: 酰化  [3,3]σ重排  水解  2-苄基吡啶氮氧化物  苯基-2-吡啶基甲醇  精细化工中间体
英文关键词: acylation  [3,3]-sigmatropic rearrangement  hydrolysis  2-benzylpyridine nitrogen-oxide  phenyl-2-pyridinyl methanol  fine chemical intermediate.
基金项目:中国博士后科学基金(2018M641642)
作者单位E-mail
荆华青 天津大学药物科学与技术学院 jing_huaqing@163.com 
李红亮 天津大学药物科学与技术学院 lhl522508@126.com 
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中文摘要:
      以2-苄基吡啶氮氧化物和三氟乙酸酐为原料,通过“一锅三步法”(串联“酰化、[3,3]σ重排和水解”反应)合成了关键药理活性中间体苯基-2-吡啶基甲醇,并对反应条件进行了优化。结果表明:当n(2-苄基吡啶氮氧化物):n(三氟乙酸酐)=1 : 1.2、N, N-二异丙基乙胺(DIPEA)为碱、甲苯为反应溶剂,室温反应6小时,经硅胶柱层析分离即可得到苯基-2-吡啶基甲醇,收率为81.0%。产物经1H NMR,13C NMR 和HRMS进行结构表征。本文以原子经济学的理念首次实现了由2-苄基吡啶氮氧化物到苯基-2-吡啶基甲醇的直接转化。
英文摘要:
      Phenyl-2-pyridinyl methanol,as a key pharmacological intermediate, was synthesized via an “one-pot three-steps” method with 2-benzylpyridine nitrogen-oxide and trifluoroacetic anhydride as starting materials, which involved tandem acylation, [3,3]-sigmatropic rearrangement and hydrolysis reaction. The reaction conditions were investigated and the optimal conditions were obtained as follows: trifluoroacetic anhydride was as acylating agent in 1.2 equivalent, N, N-diisopropylethylamine (DIPEA) was as base and the mixture was stirred in toluene for 6 h at room temperature. The phenyl-2-pyridinyl methanol was obtained by silica gel column chromatography with the yield of 81.0%, and the structures of all products were confirmed by 1H NMR,13C NMR and HRMS. This reaction firstly achieved the direct transformation from 2-benzylpyridine nitrogen-oxide to phenyl-2-pyridyl methanol in an atomic economic manner.
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