A kind of preparation method of 3-aminomethyltetrahydrofuran

A technology of aminomethyl and cyano groups, applied in the field of compound synthesis, can solve the problems of difficulty in synthesizing tetrahydrofuran compounds, unfavorable industrial production, long steps, etc., and achieve the effects of low production cost, low environmental pollution, and high utilization rate of raw materials

Active Publication Date: 2018-10-09
北京怡力生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 3-Aminomethyltetrahydrofuran is a commonly used intermediate in pharmaceuticals and pesticides. In the prior art, there are few disclosures about its preparation method. The reason is that the substitution reaction of the furan ring can be used to derive tetrahydrofuran compounds with substituents at the 2-position relatively simply. , in contrast, it is very difficult to synthesize tetrahydrofuran compounds with substituents at the 3-position; currently, only the following three methods are disclosed
However, this method has long steps and uses highly toxic sodium cyanide, which is not conducive to industrial production

Method used

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  • A kind of preparation method of 3-aminomethyltetrahydrofuran
  • A kind of preparation method of 3-aminomethyltetrahydrofuran
  • A kind of preparation method of 3-aminomethyltetrahydrofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Embodiment 1: (1) cyclization reaction

[0023]

[0024] Weigh 7.14g (0.105mol) of sodium ethoxide solid into a 250ml four-necked bottle, add 50ml of absolute ethanol to dissolve, add 11.3g (0.1mol) of ethyl cyanoacetate at 25°C, and stir at 25°C for 1 hour , a large amount of white solid appeared.

[0025] At room temperature, 5.54 g (0.126 mol) of ethylene oxide was introduced into the four-neck flask. After the introduction, the temperature was raised to 45-50° C. and stirred for 4 hours. The white solid disappeared and the system became an amber clear solution.

[0026] The whole system is subjected to vacuum distillation to remove absolute ethanol; for the distillation residue, add 50ml of pure water to the distillation residue, and adjust the pH value to 2-3 with concentrated hydrochloric acid; and extract with ethyl acetate (50ml*2) , combined the organic phases, evaporated under reduced pressure to remove ethyl acetate, and the residue continued to be rectif...

Embodiment 2

[0036] (1) Cyclization reaction

[0037] Weigh 11.78g (0.105mol) of potassium tert-butoxide solid into a 250ml four-necked bottle, add 50ml of tert-butanol to dissolve, add 11.3g (0.1mol) of ethyl cyanoacetate at 20°C, and stir at 20°C After 1 hour, a large amount of white solid appeared.

[0038] At room temperature, 5.54 g (0.126 mol) of ethylene oxide was introduced into the four-necked flask. After the introduction, the temperature was raised to 45-50° C. and stirred for 3 hours. The white solid disappeared, and the system became an amber clear solution.

[0039] The whole system is subjected to vacuum distillation to remove tert-butanol; for the distillation residue, add 50ml of pure water to the distillation residue, and adjust the pH value to 2-3 with concentrated hydrochloric acid; and extract with ethyl acetate (50ml*2) , combined the organic phases, evaporated under reduced pressure to remove ethyl acetate, and the residue continued to be rectified under reduced pre...

Embodiment 3

[0046] (1) Cyclization reaction

[0047] Weigh 7.14g (0.105mol) of sodium ethoxide solid into a 250ml four-necked bottle, add 50ml of absolute ethanol to dissolve, add 11.3g (0.1mol) of ethyl cyanoacetate at 25°C, and stir at 25°C for 1 hour , a large amount of white solid appeared.

[0048] Pass 5.54 g (0.126 mol) of ethylene oxide into the four-necked flask at 25°C. After the pass-in is complete, raise the temperature to 45-50°C and stir for 3 hours. The white solid disappears, and the system turns into an amber clear solution.

[0049] The whole system is subjected to vacuum distillation to remove absolute ethanol; for the distillation residue, add 50ml of pure water to the distillation residue, and adjust the pH value to 2-3 with concentrated hydrochloric acid; and extract with ethyl acetate (50ml*2) , combined the organic phases, evaporated under reduced pressure to remove ethyl acetate, and the residue continued to be rectified under reduced pressure; combined the organ...

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Abstract

The invention relates to a preparation method of 3-aminomethyl tetrahydrofuran. Specifically the invention relates to a method of preparing 3-aminomethyl tetrahydrofuran through reducing 3-cyano-gamma-butyrolactone. A novel synthesis technology is adopted. Ethyl cyanoacetate and ethylene oxide carry out cyclization reactions under an alkaline condition to obtain 3-cyano-gamma-butyrolactone; then 3-cyano-gamma-butyrolactone is reduced to obtain 2-aminomethyl-1,4-butylene glycol, and finally 2-aminomethyl-1,4-butylene glycol carries out dehydration and cyclization reactions to obtain 3-aminomethyl tetrahydrofuran. The synthesis technology has the advantages of easily available raw materials, simple operation, mild reaction conditions, high yield and product purity, little environmental pollution, and low production cost, is suitable for industrial massive production, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a preparation method of 3-aminomethyltetrahydrofuran, in particular to a method for preparing 3-aminomethyltetrahydrofuran by a reduction method. Background technique [0002] 3-Aminomethyltetrahydrofuran is a commonly used intermediate in pharmaceuticals and pesticides. In the prior art, there are few disclosures about its preparation method. The reason is that the substitution reaction of the furan ring can be used to derive tetrahydrofuran compounds with substituents at the 2-position relatively simply. , in contrast, it is very difficult to synthesize a tetrahydrofuran compound having a substituent at the 3-position; currently, only the following three methods are disclosed. [0003] (1) As one of the preparation methods of 3-aminomethyltetrahydrofuran, it is known to use tetrahydrofuran-3-carbaldehyde as a raw material for reductive amination in the presence of hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/14
CPCC07D307/14
Inventor 张立刚李梦菲王瑞邓旭芳陈建伟王文军
Owner 北京怡力生物科技有限公司
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