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Method for synthesizing indene compound

A technology of compounds and acids, which is applied in the field of synthesizing indenes, can solve the problems of harmful by-products, danger-prone, harsh reaction conditions, etc., and achieve the effects of high conversion rate, wide applicability, and mild reaction system

Active Publication Date: 2021-11-30
SHANGHAI BOOK CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction conditions are harsh, prone to danger, and the by-products are harmful

Method used

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  • Method for synthesizing indene compound
  • Method for synthesizing indene compound
  • Method for synthesizing indene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] In this example, 2-(o-tolyl(trimethylsilyl)methylene)-1H-indene-1,3(2H)-dione was prepared. The specific operation is as follows:

[0051]

[0052]Under nitrogen atmosphere, 2-(3-methylsilyl)propionyl)benzonitrile (0.1mmol), 2-methylphenylboronic acid (0.25mmol), [RhOH(COD) 2 ] 2 (2.5mmol%), 1,4-dioxane (2ml) and water (0.05ml) were added to a Shrek tube equipped with a magnet. The reaction was carried out at 60° C., and the reaction was monitored using a TLC plate. When 2-(3-methylsilyl)propionyl)benzonitrile was completely reacted, the heating was stopped and the reaction was cooled to room temperature. The resulting mixture was filtered through a fritted funnel, washed with dichloromethane (10 ml, 3-5 times), and then the solvent was evaporated with a rotary evaporator under low pressure to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain the desired product, 2-(o-tolyl(trimethylsilyl)methylene)-1H-indene-1,3(...

Embodiment 2

[0058] In this example, 2-((2-methoxyphenyl)(trimethylsilyl)methylene)-1H-indene-1,3(2H)-dione was prepared. The specific operation is as follows:

[0059]

[0060] Under nitrogen atmosphere, 2-(3-methylsilyl)propionyl)benzonitrile (0.1mmol), 2-methoxyphenylboronic acid (0.25mmol), [RhOH(COD) 2 ] 2 (2.5mmol%), 1,4-dioxane (2ml) and water (0.05ml) were added to a Shrek tube equipped with a magnet. The reaction was carried out at 60° C., and the reaction was monitored using a TLC plate. When 2-(3-methylsilyl)propionyl)benzonitrile was completely reacted, the heating was stopped and the reaction was cooled to room temperature. The resulting mixture was filtered through a fritted funnel, washed with dichloromethane (10 ml, 3-5 times), and then the solvent was evaporated with a rotary evaporator under low pressure to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain the desired product, 2-((2-methoxyphenyl)(trimethylsilyl)met...

Embodiment 3

[0066] In this example, 2-(naphthalen-1-yl(trimethylsilyl)methylene)-1H-indene-1,3(2H)-dione was prepared. The specific operation is as follows:

[0067]

[0068] Under nitrogen atmosphere, 2-(3-methylsilyl)propionyl)benzonitrile (0.1mmol), naphthaleneboronic acid (0.25mmol), [RhOH(COD) 2 ] 2 (2.5mmol%), 1,4-dioxane (2ml) and water (0.05ml) were added to a Shrek tube equipped with a magnet. The reaction was carried out at 60° C., and the reaction was monitored using a TLC plate. When 2-(3-methylsilyl)propionyl)benzonitrile was completely reacted, the heating was stopped and the reaction was cooled to room temperature. The resulting mixture was filtered through a fritted funnel, washed with dichloromethane (10 ml, 3-5 times), and then the solvent was evaporated with a rotary evaporator under low pressure to obtain a crude product. The crude product is purified by silica gel column chromatography to obtain the desired product, 2-(naphthalen-1-yl(trimethylsilyl)methylene)-1...

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Abstract

The invention relates to a method for synthesizing an indene compound. According to the method, a 2-(3-(silyl) propionyl) benzonitrile compound and a phenylboronic acid compound are catalyzed by metal rhodium to react. The method comprises the following steps: 1, adding a 2-(3-(silyl) propionyl) benzonitrile compound, a hydroxyl (cyclooctadiene) rhodium (I) dimer and phenylboronic acid into a drying tube with magnetons; 2, slowly adding an organic solvent in a nitrogen atmosphere, carrying out a stirring reaction at 60 DEG C, stopping the reaction after the 2-(3-(silyl) propionyl) benzonitrile derivative completely reacts, and cooling to room temperature; and 3, filtering, washing, separating and purifying the mixture obtained in the step 2 to obtain the product. The indene derivative is succeffuly synthesized at high yield, compared with other methods for synthesizing the indene derivatives, the method has the advantages that the operation is simple and convenient, and the method is suitable for synthesizing the indene derivatives with large steric hindrance. In addition, no toxic substances are added and generated in the reaction process, and an alkaline reagent does not need to be added.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing indenoid compounds. Background technique [0002] Indene is an aromatic hydrocarbon. It is a colorless transparent oily liquid at room temperature. It is extracted from coke oil with a boiling point of 182.44°C. It can be used to produce indene-coumarone resin. From the structural formula, it can be considered that it is formed by the combination of benzene ring and cyclopentadiene, so it can also be called benzocyclopentadiene. Indene is an important class of organic compounds, which is a product extracted from coke oil. Indene molecules are not aromatic and will turn black when left in the air. Cyclopentadiene in indene molecules contains an active methylene group, which can undergo various substitution reactions. The traditional synthesis method is that at 625 °C, acetonitrile is passed through activated carbon, or tetralin is passed thr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/081C07F7/083Y02P20/584
Inventor 岳燕妮邓学祖
Owner SHANGHAI BOOK CHEM CO LTD
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