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Preparation method of oxime ether

A technology of oxime ether and p-ph, applied in organic chemistry, chemical recycling, etc., can solve problems such as metal residues, environmental and human hazards, and achieve the effects of low cost, avoiding safety hazards, good ecological advantages and economic advantages

Pending Publication Date: 2022-08-02
ZHEJIANG SCI-TECH UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the process of this reaction is simple, metal catalysts are used, and metal residues are likely to be left during waste liquid treatment, which is harmful to the environment and human body.

Method used

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  • Preparation method of oxime ether
  • Preparation method of oxime ether
  • Preparation method of oxime ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Anhydrous n-butyl acetate, benzophenone oxime (0.0197g, 0.1mmol, 1.0eq), anhydrous tetrahydrofuran (0.3606g, 50eq), carbon tetrabromide (0.0597g) were sequentially added to a 5mL transparent glass reaction flask , 1.8eq), 0.1000g molecular sieve, mix well. After the magnetron was placed, the reaction flask was placed under argon for ventilation for 15 minutes, and the reaction was performed under the irradiation of a 3W LED blue light for 5 hours. After the reaction is completed, the reacted solution is placed in a centrifuge tube for centrifugation, and the upper clear liquid is taken and concentrated under reduced pressure with a rotary evaporator to obtain a thick liquid. Finally, ethyl acetate and petroleum ether were mixed in proportion as a developing solvent, and column chromatography was performed to separate the obtained product, and the yield was 87% after precipitation and drying. like figure 1 shown: 1 H NMR (400MHz, CDCl 3 )δ7.56-7.46(m,2H),7.44-7.37(m,...

Embodiment 2

[0052] 0.0189g p-trifluoromethylbenzaldehyde oxime (0.1mmol) is replaced by 0.0197g benzophenone oxime (0.1mmol), other conditions and operating procedures are the same as in Example 1, and the obtained pure product p-trifluoromethylbenzaldehyde- O-2-Tetrahydrofuryl oxime ether in 90% yield. like image 3 shown: 1 H NMR (400MHz, CDCl 3 )δ8.11(s,1H),7.72(d,J=8.2Hz,2H),7.61(d,J=8.3Hz,2H),5.90(dd,J=5.0,1.5Hz,1H),4.07– 3.93 (m, 2H), 2.18–2.02 (m, 3H), 1.93 (dt, J=9.5, 4.6 Hz, 1H). like Figure 4 shown: 13 C NMR (101MHz, CDCl 3 )δ148.54(s), 135.59(s), 125.57(dd, J=7.5, 3.7Hz), 107.00(s), 77.36(s), 77.04(s), 76.73(s), 68.14(s), 30.82(s), 23.77(s).

Embodiment 3

[0054] 0.0149g 2,4-dimethylbenzaldehyde oxime (0.1mmol) was replaced by 0.0197g benzophenone oxime (0.1mmol), other conditions and operation process were the same as in Example 1, and the obtained pure product was 2,4-dibenzophenone oxime Methylbenzaldehyde-O-2-tetrahydrofuryl oxime ether in 93% yield. like Figure 5 shown: 1 H NMR (400MHz, CDCl 3 )δ8.32(s,1H),7.64(d,J=7.8Hz,1H),6.99(d,J=9.6Hz,2H),5.92-5.86(m,1H),4.08-3.91(m,2H ), 2.38 (s, 3H), 2.31 (s, 3H), 2.16–2.00 (m, 3H), 1.97–1.86 (m, 1H). like Image 6 shown: 13 C NMR (101MHz, CDCl 3 )δ148.92(s), 139.82(s), 136.75(s), 131.47(s), 127.52(s), 127.11(s), 127.00(d, J=20.8Hz), 106.58(s), 77.39( s), 77.07(s), 76.75(s), 68.00(s), 30.87(s), 23.89(s), 21.31(s), 19.73(s).

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Abstract

The invention belongs to the technical field of synthesis of bactericides, pesticides and medicines, and particularly relates to a preparation method of oxime ether, which is characterized in that oxime is used as a raw material and is subjected to mild dehydrogenation cross-coupling reaction under the catalysis of light-mediated carbon tetrabromide to synthesize the oxime ether. The synthesis process is green and environment-friendly, the reaction system is mild, raw materials are low in price and easy to obtain, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of fungicides, pesticides and pharmaceutical synthesis, in particular to a preparation method of an oxime ether. Background technique [0002] Oxime ethers and their derivatives are important chemical products and have important uses in pesticides and medicines. Because of its high efficiency, low toxicity and low residue, it is often used as an effective group for the preparation of important new drugs and antibacterial agents. At present, there have been some reports on the synthetic methods of oxime ethers. As reported in CN109369449A, the ketoxime and the organic base are put into the autoclave in proportion, the reaction temperature is controlled between 10-60 ℃, and the alkylating reagent is passed into the reaction for 2-6h, and the filtrate is filtered after the reaction is completed. The oxime ether can be obtained by crystallization after precipitation, and the yield is about 85%. In European pa...

Claims

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Application Information

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IPC IPC(8): C07D307/20C07D313/04C07D309/10
CPCC07D307/20C07D313/04C07D309/10Y02P20/584
Inventor 涂梦沈永淼李志明王艾刘小睿
Owner ZHEJIANG SCI-TECH UNIV
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