Solvent-free preparation method for substituted cyanoacetate compound
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A cyanoacetate, solvent-free technology, applied in the field of preparation of substituted cyanoacetate, can solve the problems of low yield, organic solvent pollution, etc., and achieve the effect of green preparation method
Inactive Publication Date: 2017-10-03
XIHUA UNIV
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However, organic solvents have great pollution to the environment
This document also reports the preparation method under no catalyst and water solvent condition, but this method only has 15% productive rate in 48h reaction time, and productive rate is too low
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Embodiment 1
[0022] Embodiment 1 synthetic method of the present invention
[0023]
[0024] Add 4-bromobenzaldehyde (1) (0.2mmol, 37.0mg), ethyl cyanoacetate (2) (0.24mmol, 27.1mg), dihydropyridinate (0.24mol, 60.7mg) into a 10mL reaction tube, Raise the temperature to 100°C, stir and react for 2 hours, cool down, and then silica gel column chromatography (petroleum ether: ethyl acetate = 10:1 elution), the final product (3) is a colorless liquid with a yield of 68%, NMR The test results are as follows:
[0026] Embodiment 2 synthetic method of the present invention
[0027] 4-Bromobenzaldehyde (1) (0.2mmol, 37.0mg), ethyl cyanoacetate (2) (0.24mmol, 27.1mg), dihydropyridinate (0.24mol, 60.7) and sodium bicarbonate (0.02mmol , 1.68mg) into a 10mL reaction test tube, heated to 100 ° C, stirred for 1 hour, and then silica gel column chromatography (petroleum ether: ethyl acetate = 10:1 elution), finally a colorless liquid product (3 ), yield 72%.
Embodiment 3
[0028] The screening of base in the synthesis method of the present invention in embodiment 3
[0029] According to the method in Example 2, the present invention has screened the kind of alkaline reagent in the synthesis method, and the results are shown in Table 1.
[0030] The screening of alkaline reagent in the synthetic method of the present invention in table 1
[0031] alkaline reagent
[0032] The results show that when the synthesis method of the present invention adds alkali to the reaction raw materials, the yield is obviously better than that of the synthesis method without alkali in Example 1. Among them, DEAE and DABCO have better effects.
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Abstract
The invention discloses a solvent-free preparation method for a substituted cyanoacetate compound. The method is characterized by comprising the following steps: subjecting an aldehyde compound (I) represented by a formula shown in the description, cyanoacetate (II) represented by a formula shown in the description and a dihydropyridine ester (III) represented by a formula shown in the description to a hybrid reaction under solvent-free conditions, and carrying out separation and purification after the reaction is completed, thereby obtaining the substituted cyanoacetate (IV) represented by a formula shown in the description. According to the method, aldehydes, cyanoacetate and dihydropyridine esters serve as raw materials for the first time, and the substituted cyanoacetate can be efficiently synthesized through a one-pot method reaction without solvents and catalysts, so that the preparation method is simple, efficient and environmentally friendly.
Description
technical field [0001] The present invention relates to the preparation method of substituted cyanoacetate. Background technique [0002] Substituted cyanoacetate is an important class of pharmaceutical intermediates. The cyano group in the molecule can be easily converted into other functional groups, such as carboxylic acid, amino group, ketone, etc., and the ester group can also be easily converted into other groups. Therefore, the preparation of such compounds has very important practical value. [0003] Among them, connecting the Knoevenagel reaction and the double bond reduction reaction in series is one of the main methods for preparing substituted cyanoacetates. [0004] In order to obtain substituted cyanoacetates more conveniently, Dhevalapally B. Ramachary et al. reported a method for preparing substituted cyanoacetates in a one-pot method using cyanoacetate, ketone and dihydropyridinate as raw materials . Among them, when proline is added to catalyze and react...
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