Preparation method of beta-hydroxyphenyl selenide compound

A hydroxyphenyl compound technology, applied in the field of organic compound synthesis, can solve problems such as poor substrate universality, and achieve the effects of simple operation, high yield and mild reaction conditions

Active Publication Date: 2017-11-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the substrate has poor universality and is only suitable for phenylboronic acid with general electron-donating substituents.

Method used

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  • Preparation method of beta-hydroxyphenyl selenide compound
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  • Preparation method of beta-hydroxyphenyl selenide compound

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preparation example Construction

[0061] In the preparation method of the present invention, the reaction temperature is 100-140°C, for example, non-limitingly, 100°C, 110°C, 120°C or 140°C.

[0062] (7) Response time

[0063] In the preparation method of the present invention, the reaction time is not particularly limited. For example, the appropriate reaction time can be determined by liquid chromatography to detect the residual percentage of the target product or raw material, which is usually 2-30 hours, non-limitingly for example 2 hours, 4 hours, 6 hours, 8 hours, 10 hours, 12 hours, 14 hours, 26 hours, 28 hours or 30 hours.

[0064] (8) Separation and purification

[0065] The mixture obtained after the reaction can be further separated and purified to obtain a purer final product. Those of ordinary skill in the art are familiar with the methods of separation and purification, for example, methods such as extraction, column chromatography, distillation, decantation, filtration, centrifugation, washing...

Embodiment 1

[0069] Synthesis of 2-phenylselenylcyclohexanol

[0070]

[0071] At room temperature, aryl boronic acid (0.4mmol), selenium (1.2mmol, 3equiv), copper chloride (0.04mmol), silver nitrate (0.2mmol, 0.5equiv), reaction solvent 2mL DMSO were added to the reaction tube, at 120 Stir at the reaction temperature of ℃ for 12h; then add potassium tert-butoxide (0.8mmol, 2equiv) and ethylene oxide derivatives (1.2mmol, 3equiv) into the reaction tube, stir at the reaction temperature of 120℃ for another 12h, pass through a thin The end of the reaction was monitored by layer chromatography, and 2-phenylselenocyclohexanol was obtained after the end of the reaction.

[0072] Add 20mL of water and 10mL of ethyl acetate for extraction, then add anhydrous sodium sulfate to dry, filter after 5 minutes, wash the filter cake with ethyl acetate (5mL x 3 times), then spin off the solvent, and separate by column chromatography The product (eluent: petroleum ether: ethyl acetate = 6:1) was obtain...

Embodiment 2

[0078] Synthesis of 2-(4-methoxyphenylselenyl)cyclohexanol

[0079]

[0080] At room temperature, 4-methyl arylboronic acid (0.4mmol), selenium (2mmol, 5equiv), copper chloride (0.004mmol), silver nitrate (0.8mmol, 2equiv), reaction solvent 2mLDMSO were added in the reaction tube, in Stir at a reaction temperature of 100°C for 15h; then potassium tert-butoxide (0.2mmol, 0.5equiv) and ethylene oxide derivatives (2mmol, 5equiv) were added to the reaction tube, stirred at a reaction temperature of 100°C for another 15h, passed The end of the reaction was monitored by thin-layer chromatography to obtain 2-(4-methoxyphenylselenyl)cyclohexanol.

[0081] Add 20mL of water and 10mL of ethyl acetate for extraction, then add anhydrous sodium sulfate to dry, filter after 5 minutes, wash the filter cake with ethyl acetate (5mL x 3 times), then spin off the solvent, and separate by column chromatography The product (eluent: petroleum ether: ethyl acetate = 6:1) was obtained as a yellow...

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Abstract

The invention relates to the technical field of synthesis of organic compounds and particularly relates to a preparation method of a beta-hydroxyphenyl selenide compound. The preparation method comprises the step of with aryl boronic acid with a structure presented by a formula (I), elemental selenium and an ethylene oxide derivative presented by a formula (II) as the raw materials, and carrying out insertion reaction on elemental selenium in a reaction solvent under the common effect of a copper catalyst, silver salt and alkali, so as to obtain the beta-hydroxyphenyl selenide compound represented by a formula (III), wherein R1 and R2 are respectively independently selected from one of H, a benzene ring, a naphthalene ring, a heterocyclic ring, a substituted benzene ring, linear alkyl, branched chain, halogen, nitryl and a cyano group.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a preparation method of a β-hydroxyphenyl selenide compound. Background technique [0002] In 2010, Sangit Kumar et al. synthesized Ebselen intramolecularly with elemental Se powder under the catalysis of copper. It was the first report that Se powder participated in the catalytic cycle process, and the Se-N synthesis reaction was constructed for the first time. This method uses a one-pot approach, which greatly reduces the number of experimental steps compared to previous methods. However, there are disadvantages such as high temperature and poor compatibility of functional groups. The reaction formula is as follows: [0003] [0004] In 2014, Jin Tao Yu et al. synthesized symmetrical monoselenides using phenylboronic acid and elemental Se under copper catalysis. However, the substrate universality is poor, and it is only suitable for phenylboronic acid,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/02
CPCC07C391/02
Inventor 刘妙昌冷涛杨航黄小波高文霞吴华悦
Owner WENZHOU UNIVERSITY
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