北京大学学报(自然科学版)

γ-丁内酯α-烷基化的新方法

孟芫茹, 关烨第   

  1. 北京大学化学与分子工程学院,北京,100871
  • 收稿日期:2002-03-27 出版日期:2003-03-20 发布日期:2003-03-20

A New Method for α-Alkylation of γ-Butyrolactone

MENG Yuanru, GUAN Yedi   

  1. College of Chemistry and Molecular Enginering, Peking University, Beijing, 100871
  • Received:2002-03-27 Online:2003-03-20 Published:2003-03-20

摘要: 采用两步简单反应,顺利地得到α-取代的γ-丁内酯。首先,在醇钠存在下,严格控制反应温度为0~10℃,以内酯与芳香醛类化合物,选择性地缩合为α-烯基内酯产率40%~99%,进而采用催化转移氢化的方法,在Pd/C存在下,用NaH2PO2氢化还原上述缩合中间物,使有效地转化为α-烷基化γ-丁内酯,产率55%~99%。总体上,该方法能有效地得到目标化合物,具有方法简单易行,操作方便,反应条件温和,试剂价廉和产率相对较高的特点。

关键词: γ-丁内酯α-烷基化, 缩合, Pd/C-次亚磷酸钠, 催化转移氢化

Abstract: The α-alkylation products of γ-butyrolactone can be gained via two simple and convenient steps:(E)-α-Alkenyl-γ-butyrolactone compounds were synthesized from condensation of corresponding aromatic aldehydes and γ-butyrolactone, using common base such as MeONa and EtONa. Then the (E)-α-Alkenyl-γ-butyrolactones were reduced to α-alkyl-γ-butyrolactones by using sodium hypophosphite with Pd/C catalyst, which is named to be reaction of catalytic transfer hydrogenation.

Key words: α-alkylation of γ-butyrolactone, condensation, Pd/C-sodium hypophosphite, catalytic transfer

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