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Preparation method of 4-pentyne-1-alcohol

A technology for pentyne and chloromethyl tetrahydrofuran is applied in the field of preparing 4-pentyn-1-ol, and can solve the problems of liquid ammonia easily leaking irritating taste, danger, complicated reaction operation and the like

Inactive Publication Date: 2010-09-15
周雄飞
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

In the laboratory, the reaction operation using liquid ammonia as a solvent is more complicated, and the liquid ammonia is easy to leak and cause irritating taste, and the use of a large amount of metallic sodium has certain dangers.

Method used

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  • Preparation method of 4-pentyne-1-alcohol

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example 1

[0006] Example 1, the preparation of 4-pentyn-1-alcohol

[0007] Add 200 mL of anhydrous tetrahydrofuran to a dry 500 mL round bottom flask. The flask was cooled to minus 78 degrees Celsius in a dry ice-acetone bath, and then 62.8 mL (157.2 mmol, 2.5 mol / L) of n-butyllithium was added. 2-Chloromethyltetrahydrofuran (6.01 g, 50.7 mmol) was slowly added dropwise to this solution. The reaction temperature was controlled at minus 78 degrees, and the mixture was stirred until the thin layer chromatography showed that the reaction of the raw materials was complete. The reaction was quenched by adding saturated ammonium chloride solution, and the aqueous solution was extracted three times with ether. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and then spin-dried to obtain a crude product. The crude product was separated by column chromatography to obtain 3.9 g of 4-pentyn-1-ol, a colorless transparent liquid, with a yield of 91%.

example 2

[0008] Example two, the preparation of 4-pentyn-1-alcohol

[0009] Add 300 mL of anhydrous tetrahydrofuran to a dry 1000 mL round bottom flask. The flask was cooled to minus 78 degrees Celsius in a dry ice-acetone bath, and then 86.8 mL (217 mmol, 2.5 mol / L) of n-butyllithium was added. 2-Chloromethyltetrahydrofuran (8.3 g, 70 mmol) was slowly added dropwise to this solution. The reaction temperature was controlled at minus 78 degrees, and the mixture was stirred until the thin layer chromatography showed that the reaction of the raw materials was complete. The reaction was quenched by adding saturated ammonium chloride solution, and the aqueous solution was extracted three times with ether. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and then spin-dried to obtain a crude product. The crude product was distilled under reduced pressure to obtain 5.1 g of a colorless and transparent product, 4-pentyn-1-ol, with a yield of 87%.

[0...

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Abstract

The invention relates to a new method for synthesizing 4-pentyne-1-alcohol. In the method, 2-chloromethyl tetrahydrofuran is used as a raw material, in the presence of a lower temperature, tetrahydrofuran is used as a solvent, and n-butyllithium is used as a strong base for eliminating to obtain the 4-pentyne-1-alcohol, wherein the productivity can reach 91 percent. In the invention, the low-price raw material and a simple and convenient condition are used, and the method has higher productivity compared with the traditional method.

Description

technical field [0001] The invention relates to a method for preparing 4-pentyn-1-ol by taking 2-chloromethyltetrahydrofuran as a raw material and undergoing elimination reaction under the condition of n-butyllithium. Background technique [0002] 4-Pentyn-1-ol is a very useful chemical raw material widely used in organic synthesis. But it's very expensive, and it takes a lot of money to use it in large quantities. Organic Synthesis 1953, 33, 68-69 reported that 4-pentyn-1-ol was obtained by eliminating 2-chloromethyltetrahydrofuran as a raw material in a liquid ammonia solvent with sodium amide as a base, with a yield of 85%. The method must use liquid ammonia as a solvent, and metal sodium is dropped into the liquid ammonia to obtain sodium amide. In the laboratory, the reaction operation using liquid ammonia as a solvent is more complicated, and the liquid ammonia is easy to leak and cause irritating taste, and the use of a large amount of metallic sodium has certain ri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/042C07C29/58
Inventor 周雄飞
Owner 周雄飞
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