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A kind of addition product of acid chloride and alkyne and preparation method thereof

A technology for addition products and acid chlorides, applied in the field of addition products of acid chlorides and alkynes and its preparation, can solve the problems of lower reaction yield, side reactions, unfavorable production, etc., and achieve high yield, complex and diverse structures, and wide applications foreground effect

Active Publication Date: 2019-05-14
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The traditional addition method of acid chloride and carbon-carbon multiple bonds needs to use precious metals such as rhodium, iridium, etc., and there is a side reaction of decarbonylation in the reaction process, which reduces the reaction yield and is not conducive to industrial production.

Method used

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  • A kind of addition product of acid chloride and alkyne and preparation method thereof
  • A kind of addition product of acid chloride and alkyne and preparation method thereof
  • A kind of addition product of acid chloride and alkyne and preparation method thereof

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Embodiment 1

[0037] A kind of addition product of acid chloride and alkyne, its structural formula is:

[0038]

[0039] A kind of preparation method of the addition product of acid chloride and alkyne, described preparation method comprises the following steps:

[0040] (1) With 800mol sodium hydride as a catalyst, 200mmol diisopropyl malonate and 440mmol propargyl bromide were added to anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry, column chromatography (volume ratio ethyl acetate:petroleum ether=1:40) obtains white solid product, namely compound 1; image 3 first step reaction

[0041] (2) Mix 80mmol compound 1 with 170mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3 ) 2 Cl 2 The consumption of CuI is 0.24mmol, the consumption of CuI is 0.08mmol, with 320mmol triethylamine as base, with anhydrous aceton...

Embodiment 2

[0049] A kind of addition product of acid chloride and alkyne, its structural formula is:

[0050]

[0051]A kind of preparation method of the addition product of acid chloride and alkyne, described preparation method comprises the following steps:

[0052] (1) With 800mol sodium hydride as a catalyst, 200mmol diisopropyl malonate and 440mmol propargyl bromide were added to anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry, column chromatography (volume ratio ethyl acetate:petroleum ether=1:40) obtains white solid product, namely compound 1; Figure 7 first step reaction

[0053] (2) Mix 80mmol compound 1 with 170mmol p-chlorophenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3 ) 2 Cl 2 The consumption of CuI is 0.24mmol, the consumption of CuI is 0.08mmol, with 320mmol triethylamine as base, with anhydrou...

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Abstract

The invention discloses an acyl chloride and alkyne addition product and a preparing method thereof. The preparing method includes the steps that sodium hydride is used as a catalyst, diisopropyl malonate and propargyl bromide are added into anhydrous acetonitrile, the mixture is put in an ice-water bath and stirred for reacting, and a white solid product is obtained after purification and separation; the product phenyl ethynyl bromide is mixed in an anhydrous oxygen-free catalytic system of Pd(PPh3)2Cl2 / CuI, triethylamine is used as alkali, anhydrous acetonitrile is used as solvent, a light brown solid product is obtained through stirring reacting at the room temperature as well as purification and separation, the light brown solid product reacts with adamantanecarbonyl-chloride in methylbenzene, and the acyl chloride and alkyne addition product is obtained through purification and separation. Compared with the prior art, the prepared beta-chloro-alpha, beta unsaturated ketone does not need a metal catalyst, is high in yield and more complex and verified in structure and will show broader application prospects in chemical industry production and clinic medicine.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to an addition product of an acid chloride and an alkyne and a preparation method thereof. Background technique [0002] The high atom-economical addition of acid chlorides to carbon-carbon multiple bonds plays a very important role in organic synthesis, and this method can be used to efficiently synthesize β-chloro-α,β unsaturated ketones. β-Chloro-α,β unsaturated ketones are widely used in organic synthesis, especially the synthesis of heterocyclic compounds. [0003] The traditional addition method of acid chloride and carbon-carbon multiple bonds needs to use precious metals such as rhodium and iridium, and there is a side reaction of decarbonylation in the reaction process, which reduces the reaction yield and is not conducive to industrial production. Contents of the invention [0004] In order to solve the above technical problems, the present invention provide...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/343C07C69/757
CPCC07C67/343C07C67/347C07C69/606C07C69/757
Inventor 孟祥珍程东胡益民
Owner ANHUI NORMAL UNIV
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