A kind of synthetic method of 1-benzyloxy-2-[2-(3-methoxyphenyl) vinyl] benzene

The technology of a methoxyphenyl group and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of high processing difficulty, high risk, harsh equipment requirements, etc., and achieves the solution of great danger, simple preparation process, and difficulty in recycling. Effect

Active Publication Date: 2017-11-07
苏州诚和医药化学有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional synthesis methods such as figure 1 As shown, m-methoxybenzyl diethyl phosphate (Wittig reagent) is synthesized with triethyl phosphite and m-methoxybenzyl chloride, and a large amount or excess of triethyl phosphite is needed in the synthesis, because of High temperature reaction, and it is not very stable, the quality after recovery is poor, it cannot be reused, it is extremely difficult to handle, and the processing cost is expensive
In addition, sodium hydride is used in the process of synthesizing 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene, which is extremely dangerous, requires strict equipment, and is difficult to control. Unstable yield

Method used

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  • A kind of synthetic method of 1-benzyloxy-2-[2-(3-methoxyphenyl) vinyl] benzene
  • A kind of synthetic method of 1-benzyloxy-2-[2-(3-methoxyphenyl) vinyl] benzene

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Such as figure 2 The synthetic route shown,

[0020] 1) Synthesis of m-methoxybenzyl diphenylphosphine by Wittig reagent

[0021] Add 99.5g (0.46mol) of diphenylmethoxyphosphorus and 72g (0.42mol) of m-methoxybenzyl chloride into a 1000ml reaction flask, heat up to 55°C under stirring conditions, and keep warm at this temperature for 10 hours. Finish cooling to 10°C, and directly enter the next reaction.

[0022] 2) Synthesis of 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene

[0023] Add 25.4g (0.47mol) sodium methoxide and 300ml methanol to the above-mentioned Wittig reagent m-methoxybenzyl diphenylphosphine, control the temperature at 10°C, add 95.5g (0.45mol) of 200ml methanol solution dropwise, and the dropwise addition ends Keep the temperature at 10°C for 8 hours. After the heat preservation is over, recover methanol to dryness under reduced pressure, add 500ml of water and stir, then filter, wash the material with water until neutral, and dry at 55°C to obta...

Embodiment 2

[0026] Such as figure 2 The synthetic route shown,

[0027] 2) Synthesis of m-methoxybenzyl diphenylphosphine by Wittig reagent

[0028] Add 95.2g (0.44mol) of diphenylmethoxyphosphorus and 77g (0.45mol) of m-methoxybenzyl chloride into a 1000ml reaction flask, raise the temperature to 60°C under stirring conditions, and keep the temperature at this temperature for 12 hours. Finish cooling to 20°C, and directly enter the next reaction.

[0029] 2) Synthesis of 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene

[0030] Add 25.4g (0.47mol) sodium methoxide and 300ml methanol to the above-mentioned Wittig reagent m-methoxybenzyl diphenylphosphine, control the temperature at 20°C, add 95.5g (0.45mol) of 200ml methanol solution dropwise, and the dropwise addition ends Keep the heat preservation at 20°C for 10 hours. After the heat preservation is over, recover methanol to dryness under reduced pressure, add 500ml of water and stir, then filter, wash the material with water until ...

Embodiment 3

[0033] Such as figure 2 The synthetic route shown,

[0034] 3) Synthesis of m-methoxybenzyl diphenylphosphine by Wittig reagent

[0035] Add 99.5g (0.46mol) diphenylmethoxyphosphorus and 72g (0.42mol) m-methoxybenzyl chloride into a 1000ml reaction flask, heat up to 58°C under stirring conditions, and keep warm at this temperature for 8 hours. Finish cooling to 15°C, and directly enter the next reaction.

[0036] 2) Synthesis of 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene

[0037] Add 25.4g (0.47mol) sodium methoxide and 300ml methanol to the above-mentioned Wittig reagent m-methoxybenzyl diphenylphosphine, control the temperature at 15°C, add dropwise 95.5g (0.45mol) of 200ml methanol solution, and the dropwise addition ends Keep the temperature at 15°C for 6 hours. After the heat preservation is over, recover methanol to dryness under reduced pressure, add 500ml of water and stir, then filter, wash the material with water until neutral, and dry at 58°C to obtain 1-be...

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Abstract

The invention provides a method for synthesizing 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene. The method comprises the following steps: making diphenylmethoxyphosphine react with m-methoxybenzyl chloride at 55-60 DEG C to obtain m-methoxybenzyldiphenylphosphine oxide; adding a solvent and a basifier into the m-methoxybenzyldiphenylphosphine oxide; and keeping reactions at room temperature to obtain 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene. The synthesis preparation method is simple, mild in reaction and easy to implement.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a synthesis method of 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene. Background technique [0002] 1-Benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benzene is a drug for improving ischemic symptoms such as ulcers, pain and coldness caused by chronic arterial occlusive disease important intermediates. Traditional synthetic methods such as figure 1 Shown is the synthesis of m-methoxybenzyl diethyl phosphate (Wittig reagent) with triethyl phosphite and m-methoxybenzyl chloride. A large amount or excess of triethyl phosphite is needed in the synthesis, because of High-temperature reaction, and it is not very stable, the quality after recovery is poor, it cannot be reused, the processing is extremely difficult, and the processing cost is expensive. In addition, sodium hydride is used in the process of synthesizing 1-benzyloxy-2-[2-(3-methoxyphenyl)vinyl]benz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/215C07C41/30C07F9/53
CPCC07C41/30C07F9/5333C07C43/215
Inventor 夏秋景
Owner 苏州诚和医药化学有限公司
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