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A kind of synthetic method of β-diethyl malonate substituted tetrahydrofuran compound

A technology of diethyl malonate and tetrahydrofuran, which is applied in the synthesis field of replacing tetrahydrofuran compounds, can solve the problems of environmental pollution and low yield, and achieve the effects of simple and convenient operation, high yield and high economic benefit

Inactive Publication Date: 2016-05-04
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention will solve the problems of environmental pollution and low yield in the existing synthesis of β-diethyl malonate substituted tetrahydrofuran compounds, and provide a synthesis of β-diethyl malonate substituted tetrahydrofuran compounds method

Method used

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  • A kind of synthetic method of β-diethyl malonate substituted tetrahydrofuran compound
  • A kind of synthetic method of β-diethyl malonate substituted tetrahydrofuran compound
  • A kind of synthetic method of β-diethyl malonate substituted tetrahydrofuran compound

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specific Embodiment approach 1

[0008] Specific embodiment one: this embodiment is a synthetic method of β-diethyl malonate substituted tetrahydrofuran compounds, which is specifically completed according to the following steps:

[0009] Add enol compounds, oxidizing reagents, photoreaction catalysts, dipotassium hydrogen phosphate and dry organic solvents into the reactor, and react at room temperature for 3 to 8 hours under visible light irradiation. After the reaction is complete, add distilled water into the reaction system to obtain The mixture is then extracted with ethyl acetate as an extractant to obtain an organic phase, which is dried over anhydrous sodium sulfate and concentrated, and then purified by silica gel column chromatography with an eluent to obtain β-diethyl malonate Substituted tetrahydrofuran compounds; the molar ratio of the enol compound to the oxidizing agent is 1:(1.2~2); the molar ratio of the enol compound to the photoreaction catalyst is 1:(0.01~0.05); The mol ratio of described...

specific Embodiment approach 2

[0015] Specific embodiment two: the difference between this embodiment and specific embodiment one is: the structural formula of the enol compound is n is 1 or 2; the R 1 It is a non-heterocyclic aromatic group with an electron-donating substituent, wherein the electron-donating substituent is methyl, alkoxy or siloxy; the non-heterocyclic aromatic group is phenyl or naphthyl; the R 2 It is hydrogen, methyl, non-heterocyclic aromatic group or non-heterocyclic aromatic group with substituents, wherein the substituents are electron-withdrawing or electron-donating groups; non-heterocyclic aromatic groups are phenyl or naphthyl . Other steps are the same as in the first embodiment.

[0016] The electron-withdrawing or electron-donating groups described in this embodiment, such as halogen or alkoxy.

specific Embodiment approach 3

[0017] Embodiment 3: This embodiment differs from Embodiment 1 or Embodiment 2 in that: the oxidizing agent is diethyl bromomalonate. Other steps are the same as those in Embodiment 1 or 2.

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Abstract

The invention relates to a synthesis method for a substituted tetrahydrofuran compound, particularly a synthesis method for a beta-diethyl malonate substituted tetrahydrofuran compound. And the invention aims to solve the problems of environmental pollution and low yield in existing synthesis of beta-diethyl malonate substituted tetrahydrofuran compounds. The method includes: adding an enol compound, an oxidation reagent, a photoreaction catalyst, dipotassium hydrogen phosphate and a dry organic solvent into a reactor to carry out reaction at room temperature for 3-8h under visible light irradiation, after complete reaction, adding distilled water into the reaction system to obtain a mixture, then conducting extraction with ethyl acetate as an extraction agent to obtain an organic phase, drying and concentrating the organic phase by anhydrous sodium sulfate, and then employing an eluent to conduct silica-gel column chromatography separation and purification, thus obtaining the beta-diethyl malonate substituted tetrahydrofuran compound. The method provided by the invention has high yield and high reaction yield up to over 80%, and is suitable for synthesis of the beta-diethyl malonate substituted tetrahydrofuran compound.

Description

technical field [0001] The invention relates to a method for synthesizing substituted tetrahydrofuran compounds. Background technique [0002] β-substituted tetrahydrofuran compounds are important intermediates of fine organic synthetic chemicals such as medicines and pesticides, and have attracted extensive attention from scholars. Many synthetic methods of β-substituted tetrahydrofuran compounds have been reported one after another, most of which are based on Lewis acid or transition metal catalyst system, which will inevitably cause great pollution and damage to the environment. Moreover, tetrahydrofuran compounds substituted by diethyl malonate at the β position have not been reported yet. Therefore, it is desirable to seek a synthetic method of environmental protection, simple operation and high yield of β-diethyl malonate substituted tetrahydrofuran compounds. Contents of the invention [0003] The purpose of the present invention will solve the problems of environ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/16C07F7/18C07D309/06
CPCC07D307/16C07D309/06C07F7/1804C07F7/1892
Inventor 夏吾炯林润杨超
Owner HARBIN INST OF TECH
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