Preparation method of alpha-nitro ketoxime derivative

A technology for nitroketoxime and styrene derivatives, which is applied in oxime preparation, organic chemistry and other directions, can solve the problems of environmental pollution, expensive transition metals, and difficulty in meeting the demand for oxime compounds, and achieves environmental friendliness and shortens the reaction time. The effect of high reaction time and yield

Inactive Publication Date: 2017-12-01
佛山煜新科技有限公司
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Problems solved by technology

[0003] In some methods of synthesizing oximes reported in the prior art, most of them require the participation of transition metals, or require to be carried out under relatively high experimental conditions. On the one hand, due to the high price of transition metals, on the one hand, due to their polluting effect on the environment , it is difficult to meet the needs of chemists for oxime compounds at the present stage

Method used

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  • Preparation method of alpha-nitro ketoxime derivative
  • Preparation method of alpha-nitro ketoxime derivative
  • Preparation method of alpha-nitro ketoxime derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1-7

[0022] Example 1-7 Optimization of reaction conditions

[0023] Using styrene as the raw material, tert-butyl nitrite as the reagent, and water as the solvent (2mL), the effects of various conditions on the reaction effect were explored, and representative examples 1-7 were selected. The results are as follows Table 1 shows:

[0024]

[0025] Table I:

[0026] Example

Auxiliary (mol%)

Time(h)

T ( o C)

Yield (%)

1

—

0.5

25

12

2

—

12

25

28

3

—

24

25

62

4

—

36

25

87

5

—

48

25

84

6

PEG400 (20%)

0.5

25

91

7

PEG600 (20%)

0.5

25

89

[0027] The basic reaction conditions are as follows: 0.4 mmol styrene, 0.8 mmol tert-butyl nitrite, 2 mL water, and air.

[0028] Taking Example 1 as an example, the specific operation is as follows: Under air conditions, add styrene (0.4mmol), tert-butyl nitrite (0.8mmol) and solvent water (2mL) to a 10mL round-bottom flask reactor. Stir at room temperature for 30 minutes. After the reaction, the reaction solution was washed with saturated brine and extracted with ...

Embodiment 7

[0033]

[0034] Under air conditions, add p-chlorostyrene (0.4mmol), tert-butyl nitrite (0.8mmol), PEG400 (0.08mmol) and solvent water (2mL) into a 10mL round-bottom flask reactor, and stir for 30min at room temperature After the reaction, the reaction solution was washed with saturated brine and extracted with ethyl acetate (3x10 mL). After the organic phase was dried over anhydrous magnesium sulfate, the organic solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography to obtain the target product (Yield 83%).

Embodiment 8

[0036]

[0037] Under air conditions, add p-methoxystyrene (0.4mmol), tert-butyl nitrite (0.8mmol), PEG400 (0.08mmol) and solvent water (2mL) to a 10mL round-bottom flask reactor, at room temperature Stir for 30 min. After the reaction is complete, the reaction solution is washed with saturated brine and extracted with ethyl acetate (3x10 mL). After drying the organic phase over anhydrous magnesium sulfate, the organic solvent is removed by rotary evaporation, and the residue is separated by silica gel column chromatography. The target product (yield 87%).

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Abstract

The invention belongs to the field of organic synthesis, and specifically discloses a preparation method of alpha-nitro ketoxime derivatives. The method comprises the steps of taking a styrene derivative of the formula I-1 as a reaction raw material and butyl nitrite as a nitration reagent, adding an assistant, and reacting with water as a solvent under the condition of air at room temperature to obtain the alpha-nitro ketoxime derivative of formula I, has the characteristics of low production cost, mild process conditions, high yield, and environmentally friendly effects, and is very suitable for industrial production. The reaction formula of the method is shown in the description.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing an α-nitroketoxime derivative. Background technique [0002] As an important part of nitrogen-containing compounds, oxime compounds have a wide range of applications in the protection and deprotection of aldehydes and ketones, aldoxime dehydration to synthesize nitriles, and Beckman rearrangement reactions to synthesize amides. In addition, oxime compounds also have considerable potential in the synthesis of chiral amines and various biologically active pharmaceutical intermediates. Therefore, oxime compounds have always played an important role in the construction of complex structures of carbon-carbon and carbon-heteroatom bonds, and are one of the areas that chemists, especially natural product researchers, focus on. [0003] Most of the methods for synthesizing oximes reported in the prior art require the participation of transition metals or requi...

Claims

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Application Information

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IPC IPC(8): C07C251/48C07C249/06
CPCC07C249/06C07C251/48
Inventor 武晓云
Owner 佛山煜新科技有限公司
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