Journal of Guangxi Normal University(Natural Science Edition) ›› 2022, Vol. 40 ›› Issue (4): 154-161.doi: 10.16088/j.issn.1001-6600.2021061103

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One-pot Generation of Allylated Products from Alcohols, Carboxylic Acids and Amines with 1,3-Dibromopropane by Sodium Hydride

YIN Yudong1,2, KE Shanzhe1,2, HUANG Jiayan1,2, DENG Mengxiang1,2, LIU Guanyan1,2, CHENG Keguang1,2*   

  1. 1. State Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University),Guilin Guangxi 541004, China;
    2. School of Chemistry and Pharmacy, Guangxi Normal University, Guilin Guangxi 541004, China
  • Published:2022-08-05

Abstract: 1,3-Dibromopropane was reacted with alcohol, carboxylic acid and amine respectively to obtain a series of allyl compounds. The one-pot approach was used in this study. Firstly, estradiol as a raw material reacted with 1,3-dibromopropane under the action of alkali then the best conditions for this allylation reaction were determined. Under the best conditions, estradiol was replaced with other alcohols, carboxylic acids and amines for the reaction. The experimental results showed that the reaction of estradiol and 1,3-dibromopropane under the action of NaH alkali produced 3,17β-diallyloxyestradiol-1,3,5(10)-triene instead of 3-bromopropyl. The reaction of 1,3-dibromopropane with other alcohols, carboxylic acids and amines got higher yield of allyl ethers, allyl esters and allylamines under relatively mild conditions.

Key words: allyl ether, allylation, 1,3-dibromopropane, sodium hydride, one-pot

CLC Number: 

  • O621.3
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