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A kind of method for preparing oxalate

A technology of oxalate ester and -br, which is applied in the field of preparation of oxalate ester, can solve the problem that there is no method for synthesizing oxalate ester green, and achieve the effects of easy functional grouping, high atom economy, and mild reaction conditions

Active Publication Date: 2021-01-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] (3) Transition metal catalyzed CO and CH 3 The oxidative coupling reaction of OH can only be used to synthesize dimethyl oxalate, and the reaction requires an additional oxidant
[0007] In summary, there is no green method for synthesizing oxalate

Method used

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  • A kind of method for preparing oxalate
  • A kind of method for preparing oxalate
  • A kind of method for preparing oxalate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Add compound 1a (0.5 mmol, 101.6 mg), compound 2a (2 mmol, 224 vL), eosin Y (Eosin Y) (0.00 5 mol, 3.6 mg), N,N-dimethylformazol into a 25 mL Schlenk tube Amide (2 mL); then reacted in oxygen for 36 hours under the irradiation of a 12 W green LED lamp; after the reaction, extracted with ethyl acetate (10 mL × 3), dried over anhydrous magnesium sulfate, and removed with a rotary evaporator Solvent, silica gel adsorption, and simple column chromatography to obtain product 3a with a yield of 85%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0036] 1 H NMR (400 MHz, CDCl 3 ) δ 7.94 – 7.89 (m, 2H), 7.63 (t, J =7.4 Hz, 1H),7.50 (t, J =7.7 Hz, 2H), 5.55 (s, 2H), 4.40 (q, J =7.1 Hz, 2H), 1.40 (t, J =7.2Hz, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 189.79, 156.91, 156.88, 134,10, 133.48,128.84, 127.65, 67.59, 63.35, 13.75; HRMS (ESI...

Embodiment 2

[0038]

[0039] Add compound 1b (0.5 mmol, 114.2 mg), compound 2a (2 mmol, 224 vL), eosin Y (Eosin Y) (0.005 mol, 3.6 mg), N,N-dimethylformazol into a 25 mL Schlenk tube Amide (2 mL). Then the system was reacted in oxygen for 36 hours under the irradiation of 12 W green LED lamp. After the reaction, it was extracted with ethyl acetate (10 mL × 3), dried over anhydrous magnesium sulfate, the solvent was removed by a rotary evaporator, adsorbed on silica gel, and the product 3b was obtained by simple column chromatography with a yield of 73%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0040] 1 H NMR (400 MHz, CDCl 3 ) δ 8.03-7.97 (m, 1H), 7.66-7.59 (m, 1H), 7.33-7.27 (m, 1H), 7.24-7.17 (m, 1H), 5.43 (d, J =3.7 Hz, 2H), 4.42 (q, J =7.1 Hz,2H), 1.42 (t, J =7.2 Hz, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 188.00, 187.97,163.65, 161.12, 157.04,...

Embodiment 3

[0042]

[0043] Add compound 1c (0.5 mmol, 119.5 mg), compound 2a (2 mmol, 224 vL), eosin Y (Eosin Y) (0.005 mol, 3.6 mg), N,N-dimethylformazol into a 25 mL Schlenk tube Amide (2 mL). Then the system was reacted in oxygen for 36 hours under the irradiation of 12 W green LED lamp. After the reaction, it was extracted with ethyl acetate (10 mL × 3), dried over anhydrous magnesium sulfate, the solvent was removed by a rotary evaporator, adsorbed on silica gel, and the product 3c was obtained by simple column chromatography with a yield of 90%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

[0044] 1 H NMR (400 MHz, CDCl 3 ) δ 7.50-7.36 (m, 3H), 7.18-7.13 (m, 1H), 5.52(s, 2H), 4.40 (q, J =7.1 Hz, 2H), 3.84 (s, 3H), 1.40 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 189.64, 159.82, 156.88, 134.69, 129.82, 120.47, 119.98, 111.95, 67.63, 63.29, 55.27,...

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Abstract

The invention discloses a method for preparing oxalate: using diazo compounds and α-Br ketones as reaction substrates, and using O 2 As oxygen source and oxidizing agent, visible light is used as energy source, organic dye is used as photocatalyst, and oxalate is obtained through free radical process in organic solvent. The method used in the present invention has the following characteristics: the reaction is more environmentally friendly and economical, the substrate has wider applicability, the later functional group is easier, the reaction condition is mild, it can be carried out in the air, the amount of photocatalyst is less, and the post-treatment is simple. At the same time, the reactants, photocatalysts and other raw materials used in the present invention are cheap and easy to obtain, the reaction composition is reasonable, no ligand is needed, the atom economy is high, the reaction steps are few, and a higher yield can be obtained with only one step of reaction, which is in line with contemporary green The requirements and direction of chemistry and sustainable development are suitable for the synthesis of asymmetrically substituted oxalates that are difficult to synthesize by traditional methods.

Description

technical field [0001] The invention relates to a method for preparing oxalate, belonging to the technical field of organic synthesis. Background technique [0002] Oxalate is widely found in natural products and drug molecules, and is also a common structural unit in organic synthesis. At present, there are many methods for preparing oxalate, but each method has some disadvantages. For example: [0003] (1) The traditional use of oxalyl chloride or oxalyl monochloride to react with alcohol or ether requires base catalysis. Among them, oxalyl chloride is not only sensitive to air, afraid of moisture, but also highly toxic and corrosive. The synthesized oxalate can only be For symmetrically substituted oxalate esters, if oxalyl monochloride is used as a raw material, oxalyl monochloride needs to be prepared first, and this step is difficult to control and the synthesis is troublesome; [0004] (2) Transesterification with oxalate to synthesize new oxalate; [0005] (3) Tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/00C07C67/18C07C69/36
CPCC07C67/00C07C67/18C07D307/42C07C69/36
Inventor 万小兵马美华郝伟伟马亮郑永高廉鹏程
Owner SUZHOU UNIV
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