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A kind of preparation method of trans-type disubstituted olefin

A double-substituted, olefinic technology, applied in the direction of organic chemistry, can solve problems such as a large amount of metal waste, expensive catalysts and high-temperature reaction conditions

Active Publication Date: 2021-08-20
安迪克森医药科技河北有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems that the current preparation process of disubstituted olefins produces a large amount of metal waste and requires expensive catalysts and high-temperature reaction conditions, the present invention provides a method for preparing trans-type disubstituted olefins

Method used

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  • A kind of preparation method of trans-type disubstituted olefin
  • A kind of preparation method of trans-type disubstituted olefin
  • A kind of preparation method of trans-type disubstituted olefin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This example provides a preparation method of trans-disubstituted olefin 3a:

[0032] Its synthetic route is:

[0033]

[0034] 2-Methylquinoline (1mmol), benzyl alcohol (2.5mmol), TEMPO (0.1mmol), Fe(NO 3 ) 3 9H 2 O (0.1 mmol) and t-BuOK (2 mmol) were sequentially added to a flask containing 2 mL of THF, the air in the flask was replaced with oxygen, then stirred at 50°C, and the reaction process was monitored by thin-layer chromatography. After the reaction was complete, it was quenched with water (10 mL).

[0035] The reaction product was extracted with ethyl acetate (3×20 mL), washed with saturated brine (20 mL), washed with anhydrous Na 2 SO 4 After drying, filtering, and concentrating the obtained filtrate, 196.6 mg was obtained by silica gel column chromatography (200-300 mesh, the developing solvent was a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 10:1), and the yield was 85%.

[0036] Gained product is carried out nuclea...

Embodiment 2

[0039] This example provides a preparation method of trans disubstituted olefin 3b:

[0040] The synthetic route is:

[0041]

[0042] 2-methylpyrazine (1mmol), benzyl alcohol (2.5mmol), TEMPO (0.1mmol), Fe(NO 3 ) 3 9H 2 O (0.1 mmol) and t-BuOK (2 mmol) were sequentially added to a flask containing 2 mL of THF, the air in the flask was replaced with oxygen, then stirred at 50°C, and the reaction process was monitored by thin-layer chromatography. After the reaction was complete, it was quenched with water (10 mL).

[0043] The reaction product was extracted with ethyl acetate (3×20 mL), washed with saturated brine (20 mL), washed with anhydrous Na 2 SO 4 After drying, filtering, and concentrating the obtained filtrate, 136.7 mg of the product was obtained by silica gel column chromatography (200-300 mesh, the developing solvent was a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 15:1), and the yield was 75%.

[0044] Gained product is carr...

Embodiment 3

[0047] This example provides a preparation method of trans disubstituted olefin 3c:

[0048] Its synthetic route is:

[0049]

[0050] 2-Methylquinoline (1mmol), piperonyl alcohol (2.5mmol), TEMPO (0.1mmol), Fe(NO 3 ) 3 9H 2 O (0.1 mmol) and t-BuOK (2 mmol) were sequentially added to a flask containing 2 mL of THF, the air in the flask was replaced with oxygen, then stirred at 50°C, and the reaction process was monitored by thin-layer chromatography. After the reaction was complete, it was quenched with water (10 mL).

[0051] The reaction product was extracted with ethyl acetate (3×20 mL), washed with saturated brine (20 mL), washed with anhydrous Na 2 SO 4 After drying, filtering, and concentrating the obtained filtrate, 123.9 mg of the product was obtained by silica gel column chromatography (200-300 mesh, the developing solvent was a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 20:1), and the yield was 45%.

[0052] Gained product is ca...

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Abstract

The invention relates to the technical field of organic chemical synthesis, in particular to a method for preparing trans-type disubstituted olefins. The preparation method uses primary alcohol and methyl nitrogen heterocyclic ring as raw materials, uses transition metal salt, nitrogen oxide and alkali as catalyst, and uses organic solution as reaction medium to react in an oxygen atmosphere. The reaction by-product of the preparation method is only water, which does not pollute the environment, the required transition metal catalyst is cheap and easy to obtain, the reaction does not require high temperature, and the reaction cost and requirements on reaction conditions can be reduced.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of trans-type disubstituted olefins. Background technique [0002] Alkene group is a common pharmacophore, which widely exists in various natural products and synthetic drugs with physiological activity, and is also a fragment that constitutes various functional materials. As an important fine chemical, olefins containing olefin groups are widely used in industries such as pesticides, medicines, and spices. For example, a disubstituted olefin, montelukast, is indicated for the prophylaxis and long-term treatment of asthma, including prevention of daytime and nocturnal asthma symptoms. [0003] There are many traditional methods for synthesizing disubstituted olefins: (1) classic name reaction (Horner-Wadsworth-Emmons, etc.); (2) catalytic Heck reaction and Suzuki coupling reaction; (3) olefin metathesis reaction. Although thes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D241/12C07D405/06C07D215/12C07D409/06C07D401/06C07D215/18C07D215/20C07D215/14
CPCC07D215/06C07D215/12C07D215/14C07D215/18C07D215/20C07D241/12C07D401/06C07D405/06C07D409/06
Inventor 张志光张勇李玲戴思伟李星稀
Owner 安迪克森医药科技河北有限公司
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