“一锅三步法”合成苯基-2-吡啶基甲醇
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中国博士后科学基金(2018M641642)


Synthesis of phenyl-2-pyridyl methanol by “one-pot three-steps” method
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The 64th China Postdoctoral Science Foundation Grant (No.2018M641642)

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    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。

    Abstract:

    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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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(10):0

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  • 收稿日期:2020-03-23
  • 最后修改日期:2020-04-28
  • 录用日期:2020-05-06
  • 在线发布日期: 2020-06-30
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