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Method for synthesizing 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran

A technology of tetramethyl julolidine and dinitrile methylene is applied in the field of synthesis of -4-dinitrile methylene-2-tert-butyl-6-pyran, and can solve the problems of long reaction time and the like , to achieve the effect of good purity and shorten the purification cycle

Inactive Publication Date: 2012-02-01
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction time of this method is longer, and the reaction yield and product purity purification still need to be further improved.

Method used

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  • Method for synthesizing 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran
  • Method for synthesizing 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran
  • Method for synthesizing 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The present invention is implemented according to the following synthetic route:

[0021]

[0022] In a 100ml round bottom flask equipped with an air condenser, add 2.14g (0.01mol) of 2-methyl-6-tert-butyl-4-dicyanomethenyl-4H-pyran, 9-formyl-1 , 2.57g (0.01mol) of 1,7,7-tetramethyljulonidine, 55ml (1.0mol) of glycerol, and 3.0ml (0.03mol) of piperidine, after making it uniformly mixed at room temperature, added to In the microwave reactor, heat up to the reflux state for 2 minutes, the thin-layer chromatography detects that the reaction is complete, stop the reaction, cool the reaction solution to room temperature, filter, wash the filter cake with 30ml of absolute ethanol, repeat 3 times, dry the filter cake, and obtain (E)-4-Dinitrilemethylene-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidine vinyl)pyran. Then the vacuum is 1.0×10 -3 pa, the temperature is 220°C, after sublimation and purification, 3.85 g of red solid was obtained with a yield of 85% and a purity of...

Embodiment 2

[0027] In a 100ml round bottom flask equipped with an air condenser, add 2.14g (0.01mol) of 2-methyl-6-tert-butyl-4-dicyanomethenyl-4H-pyran, 9-formyl-1 , 3.86g (0.015mol) of 1,7,7-tetramethyljulolidine, 66ml (1.2mol) of glycerol, 3.0ml (0.03mol) of piperidine, after making it uniformly mix at room temperature, add to In the microwave reactor, heat up to the reflux state for 2 minutes, the thin-layer chromatography detects that the reaction is complete, stop the reaction, cool the reaction solution to room temperature, filter, wash the filter cake with 30ml of absolute ethanol, repeat 3 times, dry the filter cake, and obtain (E)-4-Dinitrilemethylene-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidine vinyl)pyran. Then the vacuum is 1.0×10 -3 pa, the temperature is 220° C., after sublimation and purification, 3.86 g of a red solid was obtained, with a yield of 85.2% and a purity of 99.6%.

Embodiment 3

[0029] In a 100ml round bottom flask equipped with an air condenser, add 3.21g (0.015mol) of 2-methyl-6-tert-butyl-4-dicyanomethenyl-4H-pyran, 9-formyl-1 , 2.57g (0.01mol) of 1,7,7-tetramethyljulonidine, 55ml (1.0mol) of glycerol, and 5.0ml (0.05mol) of piperidine, after making it uniformly mixed at room temperature, added to In the microwave reactor, heat up to the reflux state for 2 minutes, the thin-layer chromatography detects that the reaction is complete, stop the reaction, cool the reaction solution to room temperature, filter, wash the filter cake with 30ml of absolute ethanol, repeat 3 times, dry the filter cake, and obtain (E)-4-Dinitrilemethylene-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidine vinyl)pyran. Then the vacuum is 1.0×10 -3 pa, the temperature is 220° C., after sublimation and purification, 3.86 g of a red solid was obtained, with a yield of 85.2% and a purity of 99.6%.

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Abstract

The invention discloses a method for synthesizing 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran. The structural formula of 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran is shown in the specifications. The method comprises the following steps of: uniformly mixing 2-methyl-6-tert-butyl-4-dicyanomethylene-4H-pyran, 9-formyl-1,1,7,7-tetramethyljulolidine, glycerol and piperidine in the molar ratio of (1.5:1:100:3)-(1:1.5:120:5) at room temperature; adding the mixture into a microwave reactor; heating for 2-3 minutestill refluxing; cooling to room temperature; filtering; washing a filter cake with absolute alcohol and drying; and sublimating to obtain 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran. The method is used for preparing 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran.

Description

technical field [0001] The present invention relates to a kind of synthetic method, relate in particular to a kind of (E)-4-dinitrile methylene-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidine ethylene Base) pyran (DCJTB) synthetic method. Background technique [0002] Organic Light-Emitting Diode (OLED) has self-illumination, wide viewing angle, fast response, thinner and lighter, stable image, high resolution, rich colors, high luminous efficiency, low energy consumption, applicable temperature It has excellent characteristics such as wide range, strong shock resistance, low cost, and flexible display. It has broad application prospects in the fields of communication, lighting, commerce, transportation, computers, electronic products, and industrial applications. It is considered to be the most ideal and most ideal. A promising third-generation display technology. [0003] The performance of organic electroluminescent devices mainly depends on the light-emitting materials. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
Inventor 徐茂梁张创军王子俊封利民胡琳琳宋新潮张倩
Owner XIAN MODERN CHEM RES INST
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