Synthesis method of end-group alkyne

A synthesis method and terminal alkyne technology, which is applied in chemical instruments and methods, preparation of hydroxyl compounds, hydrocarbons, etc., can solve the problems of high risk and high equipment requirements, and achieve simple operation, high equipment requirements, and high yield Effect

Active Publication Date: 2010-10-20
SHANGHAI RUIYI MEDICAL TECH
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, terminal acetylene derivatives have been widely used in pharmaceutical and chemical industries, and the traditional synthesis method is to obtain acetylene gas in liquid ammonia at -78 degrees by nucleophilic substitution reaction. This method requires high equipment and is dangerous. Big

Method used

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  • Synthesis method of end-group alkyne

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preparation example Construction

[0020] A kind of synthetic method of terminal alkynes of the present invention comprises the following steps:

[0021] a. Add the reaction solvent and acetylene lithium ethylenediamine into the flask, cool down to -10-10°C after the solution is clarified, and then add some solvent;

[0022] b, add haloalkane, and control the reaction temperature below 20°C;

[0023] c, 0.5~5h after dripping;

[0024] d, add a large amount of water in the reaction bottle to quench the reaction, separate the liquids, wash with a large amount of water several times, and separate the liquids;

[0025] e, Atmospheric distillation, collecting fractions near the boiling point of the product to obtain the product.

[0026] Its reaction formula is as follows:

[0027]

[0028] In the above reaction formula, X is a halogen, R is an alkyl group, a hydroxyl group, a carboxyl group, and n is 1-8.

[0029] Acetylene lithium ethylenediamine in the above-mentioned preparation method is prepared through...

Embodiment 1

[0035] 1-Hexyne

[0036] (1) Add 50ml DMSO and acetylene lithium ethylenediamine to the reaction flask, and cool down to 10°C after the solution is clarified;

[0037] (2) Add bromobutane dropwise, the molar ratio of bromobutane and acetylene lithium ethylenediamine is 1:1, the heat release is fast, use ice water to cool down, control the reaction temperature to 10-20°C, and add dropwise for 30min;

[0038] (3) After dripping, react at room temperature for 1 hour;

[0039] (4) Add 10% sulfuric acid solution dropwise, adjust pH<7, then add 50ml of water for phase separation;

[0040] (5) Separate the upper oil phase, wash twice with 20 ml of saturated sodium chloride, separate the phases, and dry the organic phase;

[0041] (6) Atmospheric distillation, collecting fractions at about 70-72°C.

Embodiment 2

[0043] 5-Chloro-1-pentyne

[0044] (1) Add 1,3-bromochloropropane and tetrahydrofuran into a 50L kettle, and cool down to -10°C.

[0045] (2) Add the DMSO solution of acetylene lithium ethylenediamine dropwise, so that the molar ratio of 1,3-bromochloropropane to acetylene lithium ethylenediamine is 1:2, the reaction releases heat quickly, stir vigorously, and control the temperature T<-10 ℃.

[0046] (3) The dripping is completed within 2-3 hours, and after the dripping is completed, T<-10°C for 2 hours.

[0047] (4) After the reaction is completed, add water to extract the reaction, stir and let stand to separate layers, wash the upper oil phase with a large amount of water until the organic phase is about 1.5 L, and dry over anhydrous sodium sulfate.

[0048] (5) Atmospheric distillation to obtain the product.

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Abstract

The invention relates to a synthesis method of end-group alkyne, which comprises the steps of: mixing solvent and lithium acetylide ethylenediamine; cooling the solution to -10 to 10 DEG C when the solution is clear, and then adding haloalkane into the cooled solution; leading the molar ratio between the lithium acetylide ethylenediamine and the haloalkane to be 1: 1-2: 1, and controlling the temperature to be -20 to 20 DEG C and the reaction time to be 0.5-5h; and finally, extracting, washing, distilling, collecting fraction with the boiling point close to that of the product, and obtaining a finished product. Compared with the prior art, the synthesis method has the advantages of simple method, convenient operation, high yield and the like.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate, in particular to a method for synthesizing a terminal alkyne. Background technique [0002] In recent years, terminal acetylene derivatives have been widely used in pharmaceutical and chemical industries, and the traditional synthesis method is to obtain acetylene gas in liquid ammonia at -78 degrees by nucleophilic substitution reaction. This method requires high equipment and is dangerous. big. Contents of the invention [0003] The object of the present invention is to provide a method for synthesizing a terminal alkyne with simple method, convenient operation and high yield in order to overcome the above-mentioned defects in the prior art. [0004] The purpose of the present invention can be achieved through the following technical solutions: a synthetic method of a terminal alkyne, characterized in that the method is to mix the solvent with acetylene lithium ethyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C11/22C07C1/32C07C21/22C07C17/263C07C57/18C07C51/353C07C33/042C07C29/34
Inventor 薛嵩
Owner SHANGHAI RUIYI MEDICAL TECH
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