Preparation method of 5-hydroxy-7,7-dimethyl-2H-indanone

Abstract

The invention discloses a preparation method of 5-hydroxy-7,7-dimethyl-2H-indanone. The method is achieved through the following steps: 1) cooling a tetrahydrofuran solution of methyl 3,3-dimethyl-4-pentenoate and dropwise adding a reducing agent and stirring so as to obtain 3,3-dimethyl-4-pentenol; 2) adding an oxidizing agent to the 3,3-dimethyl-4-pentenol and stirring and reacting to obtain 3,3-dimethyl-4-pentenal; 3) adding an ether solution of3,3-dimethyl-4-pentenal into an ether solution of magnesium propargyl bromide and stirring and reacting to obtain 5,5-dimethyl-6-ene-1-alkyne heptanol; and 4) adding cobalt carbonyl into a dichloromethane solution of 5,5-dimethyl-6-ene-1-alkyne heptanol and stirring and reacting, adding N-methyl morpholine oxide and continuously reacting to obtain the target product. The raw materials used in the method are simple and easily available; the preparation method is simple; the operation steps are simple; and synthesis cost is low.

Description

technical field [0001] The invention belongs to the technical field of natural product synthesis, and relates to a preparation method of 5-hydroxy-7,7-dimethyl-2H-indanone. Background technique [0002] 5-Hydroxy-7,7-dimethyl-2H-indanone is an important [4.3.0]bicyclic compound whose unique molecular structure exists in many active natural products and can be used as a Advanced synthetic intermediates; such as jiadifenone (Miwa Kubo, Kana Kobayashi, Jian-Mei Huang, Kenichi Harada, Yoshiyasu Fukuyama Tetrahedron Letters 2012, 53, 1231–1235.) There is no report on the synthesis of this compound, and this case is 5- Hydroxy-7,7-dimethyl-2H-indanone provides a simple and practical preparation method. Contents of the invention [0003] In view of this, the object of the present invention is to provide a preparation method of 5-hydroxyl-7,7-dimethyl-2H-indanone. [0004] In order to achieve the above object, the technical scheme of the present invention is achieved in that a k...

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Problems solved by technology

[0002] 5-Hydroxy-7,7-dimethyl-2H-indanone is an important [4.3.0]bicyclic compound whose unique molecular structure exists in many active natural products and can be used as a Advanced synthetic intermediates; such as jiadifenone (Miwa Kubo, Kana Kobayashi, Jian-Mei Huang, Kenichi Harada, Yoshiyasu Fukuyama Tetrahedron Letters 2012, 53, 1231–1235.) There is no report on the synthesis of this compound, and this case is 5- Hydroxy-7,7-dimethyl-2H-indanone provides a simple and practical preparation method

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