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Green preparation method of alpha-hydroxyketone

A green technology for hydroxyketones, applied in the field of green preparation of α-hydroxyketones, to achieve the effects of wide application of substrates, simple and easy method, convenient and safe operation

Active Publication Date: 2018-05-29
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the direct α-hydroxylation of α-methylene ketone driven by visible light has not been reported

Method used

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Examples

Experimental program
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Effect test

preparation example Construction

[0017] Preparation method of the present invention can represent with following typical reaction formula:

[0018]

Embodiment 1

[0019] Example 1 A green preparation method of α-hydroxy ketone, the method refers to sequentially adding 0.3 mmol of 1-phenyl-1-propanone, 0.06 mmol of iodine, 1,4-diazabicyclo[2.2.2]octane Add 0.15 mmol of alkane (DABCO) and 2.0 mL of methanol into a 5 mL glass reaction vial; then, under the irradiation of a 23 W compact fluorescent lamp (CFL), stir the reaction at room temperature for 24 h in an air atmosphere to obtain a reaction mixture. Separation by silica gel column chromatography yielded 34.5 mg of 1-phenyl-2-hydroxyl-1-propanone, whose structural formula is as follows:

[0020] .

[0021] Among them: the mobile phase used in the silica gel column chromatography separation is a mixed solution obtained by mixing PE and EtOAc at a ratio of 10 mL:1 mL.

[0022] The analysis results of the obtained product 1-phenyl-2-hydroxy-1-propanone are as follows: colorless liquid; yield 77%. 1 H NMR (600 MHz, CDCl 3 ): δ 7.92 (d, J = 8.4 Hz, 2H), 7.61 (t, J = 7.2 Hz, 1H), 7...

Embodiment 2

[0023] Example 2 A green preparation method of α-hydroxy ketone, the method refers to sequentially adding 0.3 mmol of 1-p-tolyl-1-propanone, 0.06 mmol of iodine, 1,4-diazabicyclo[2.2.2] Octane 0.15 mmol (DABCO) and methanol 2.0 mL were added to a 5 mL glass reaction bottle; then under the irradiation of a 23 W compact fluorescent lamp (CFL), the reaction was stirred at room temperature in an air atmosphere for 27 h to obtain a reaction mixture, which was subjected to Silica gel column chromatography to obtain 30.5 mg of 1-p-tolyl-2-hydroxyl-1-propanone, whose structural formula is as follows:

[0024] .

[0025] Among them: the mobile phase used in the silica gel column chromatography separation is a mixed solution obtained by mixing PE and EtOAc at a ratio of 15 mL:1 mL.

[0026] The analysis results of the obtained product 1-p-tolyl-2-hydroxyl-1-propanone are as follows: light yellow liquid, yield 62%. 1 HNMR (600 MHz, CDCl 3 ): δ 7.82 (d, J = 8.4 Hz, 2H), 7.29 (d, J...

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Abstract

The invention relates to a green preparation method of alpha-hydroxyketone. The method comprises the following steps: adding ketone, iodine, 1,4-diazabicyclo[2.2.2]octane and methanol into a glass reaction bottle in sequence; then stirring and reacting for 14 to 30h at room temperature in an air atmosphere under the irradiation of a 23W compact type fluorescent lamp, so as to obtain a reaction mixture; carrying out silica gel column chromatographic separation to obtain the pure alpha-hydroxyketone. The green preparation method provided by the invention has the characteristics of greenness, high efficiency, simplicity in operation, moderate conditions, wide applicability and easiness for industrialization.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a green preparation method of alpha-hydroxy ketones. Background technique [0002] α-Hydroxyketones (also known as azoin) are not only important structural units of many natural products and bioactive compounds, but also important intermediates in organic synthesis and pharmaceutical synthesis. Therefore, scientists have developed a large number of methods for synthesizing such compounds. [0003] Among the methods for the preparation of α-hydroxy ketones, the most commonly used methods include azoin condensation of aldehydes, α-hydroxylation of ketones, ketone hydroxylation of alkenes, reduction of 1,2-diketones and selectivity of vicinal diols. oxidation. In addition, they are often prepared by oxidation of pre-prepared enolates or silyl enolates with N-oxides or organic peroxides. In contrast, the direct oxidative α-hydroxylation of ketones is undoubtedly the most...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/64C07C49/82C07C49/84C07C49/83C07D333/22C07D317/54
CPCC07C45/64C07D317/54C07D333/22C07C49/82C07C49/84C07C49/83Y02B20/00
Inventor 杨靖亚谢栋泰周红艳李政
Owner NORTHWEST NORMAL UNIVERSITY
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