Method for preparing 4,4-pyran diethyl dicarboxylate derivative

A technology of diethylpyranedicarboxylate and diethylmalonate, which is applied in the field of synthesis of photoresist materials, can solve the problems of limited wide application, long reaction time, and low reaction yield, and achieve cheap and easy raw materials. High efficiency, short reaction time and simple operation

Active Publication Date: 2015-09-16
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Similar compounds are generally based on sodium ethoxide, sodium hydride, and potassium carbonate, and the addition of dihaloethyl ether or diethyl malonate is added dropwise, but these synthetic methods have a long reaction time and complicated operation, and the reaction yield is low. Low and many other disadvantages limit the wide application of this type of compound

Method used

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  • Method for preparing 4,4-pyran diethyl dicarboxylate derivative
  • Method for preparing 4,4-pyran diethyl dicarboxylate derivative
  • Method for preparing 4,4-pyran diethyl dicarboxylate derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Example 1 Preparation of 4,4-diethyl pyrandicarboxylate (sodium tert-amylate is the base)

[0020] Add 48.0g (0.3mol) of diethyl malonate, 42.6g (0.3mol) of dichloroethyl ether, 480g of dry DMF, and 0.6g of cuprous iodide to a 1L three-necked flask protected by nitrogen, and the obtained system is light yellow and transparent solution. The temperature was raised to 100°C with stirring. A DMF solution of sodium tert-amyloxide (prepared from 69.3g sodium tert-amyloxide and 277.2g DMF) was added dropwise. Refluxed for 2 hours, followed by GC until no raw material remained, evaporated the solvent under reduced pressure, and continued to distill under reduced pressure to obtain 61.5 g of colorless liquid, yield: 89.1%.

[0021] 1H NMR (CDCl 3 , TMS, 500MHz): 4.121-4.132 (q, 4H), 1.842-1.851 (m, 4H), 1.124-1.138 (t, 6H); GC-MS: 229 (M+).

[0022]

Embodiment 2

[0023] Example 2 Preparation of 4,4-diethyl pyrandicarboxylate (sodium tert-butoxide is the base)

[0024] Add 48.0g (0.3mol) of diethyl malonate, 42.6g (0.3mol) of dichloroethyl ether, 480g of dry DMF, and 0.6g of cuprous iodide to a 1L three-necked flask protected by nitrogen, and the obtained system is light yellow and transparent solution. The temperature was raised to 100°C with stirring. A DMF solution of 60.5 g of sodium tert-butoxide (prepared from 60.5 g of sodium tert-butoxide and 202 g of DMF) was added dropwise. Refluxed for 2 hours, followed by GC until there was no raw material left, the solvent was evaporated under reduced pressure, and the distillation was continued under reduced pressure to obtain 58.0 g of a colorless liquid, yield: 84.1%.

[0025] 1H NMR (CDCl 3 , TMS, 500MHz): 4.121-4.132 (q, 4H), 1.842-1.851 (m, 4H), 1.124-1.138 (t, 6H); GC-MS: 229 (M+).

[0026]

Embodiment 3

[0027] Example 3 Preparation of 4,4-diethyl pyrandicarboxylate (potassium tert-butoxide is the base)

[0028] Add 48.0g (0.3mol) of diethyl malonate, 42.6g (0.3mol) of dichloroethyl ether, 480g of dry DMF, and 0.6g of cuprous iodide to a 1L three-necked flask protected by nitrogen, and the obtained system is light yellow and transparent solution. The temperature was raised to 100°C with stirring. A DMF solution of 71.2 g of potassium tert-butoxide (prepared from 71.2 g of potassium tert-butoxide and 284.8 g of DMF) was added dropwise. Refluxed for 2 hours, followed by GC until no raw material was left, the solvent was evaporated under reduced pressure, and the distillation was continued under reduced pressure to obtain 59.5 g of colorless liquid, yield: 86.2%.

[0029] 1H NMR (CDCl 3 , TMS, 500MHz): 4.121-4.132 (q, 4H), 1.842-1.851 (m, 4H), 1.124-1.138 (t, 6H); GC-MS: 229 (M+).

[0030]

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Abstract

The invention relates to a method for preparing 4,4-pyran diethyl dicarboxylate and a derivative thereof. According to the invention, diethyl malonate and substituted dichloroethyl ether are adopted as raw materials; cuprous iodide is used for catalyzing; one or a mixture of compounds selected from potassium tert-butoxide, sodium tert-butoxide and sodium tert-pentoxide is adopted as an alkali, and a reaction is carried out; when the reaction is finished, a solvent is removed by reduced-pressure distillation; and reduced-pressure distillation is continued, such that 4,4-pyran diethyl dicarboxylate or the derivative thereof are obtained. The method provided by the invention has never been reported before. The raw materials are easy to obtain, the reaction method is simple and feasible, and the reaction time is short. The method has high application and market values.

Description

technical field [0001] The invention relates to a method for preparing diethyl 4,4-pyrandicarboxylate and derivatives thereof, and belongs to the field of synthesis of photoresist materials. Background technique [0002] In recent years, China's microelectronics and flat panel display industries have developed rapidly, driving the establishment and development of related supporting enterprises in the industrial chain such as photoresist materials. In particular, the rapid development of LED (light emitting diode) in 2009 has more effectively promoted the development of the photoresist industry. On the basis of the original discrete devices, IC, and LCD (liquid crystal display), China's photoresist industry market has added LEDs, coupled with the potential market for photovoltaics. By 2010, China's photoresist market will exceed 2 billion yuan. Accounting for more than 10% of the international photoresist market. [0003] During the imaging process of the photoresist, due t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/08C07D309/10
CPCC07D309/08C07D309/10
Inventor 李永刚王正张旭辉林少波朱晓利邢杜庆
Owner VALIANT CO LTD
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