One pot method for preparing aryl-alpha-keto ester based on arylethyl ketone

A technology of aryl ethyl ketone and keto ester, which is applied in the preparation field of organic chemical technology, can solve the problems of high synthesis cost, difficulty in obtaining aryl acetate, difficult reaction operation, etc., and achieve low synthesis cost and high source of raw materials Convenience and high reaction yield

Inactive Publication Date: 2010-02-10
SHANGHAI JIAO TONG UNIV +1
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method is also a one-pot method, the raw materials used, aryl acetate, are not easy to get, and the reagents involved in the reaction are such as: 4-acetamidobenzenesulfonic acid diazonium used in the transfer of the diazo group, and the

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  • One pot method for preparing aryl-alpha-keto ester based on arylethyl ketone
  • One pot method for preparing aryl-alpha-keto ester based on arylethyl ketone
  • One pot method for preparing aryl-alpha-keto ester based on arylethyl ketone

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Embodiment 1

[0024] Such as figure 1 Shown, the present embodiment preparation method comprises the following steps:

[0025] Under nitrogen protection, acetophenone (0.48g, 4.0mmol), selenium dioxide (0.66g, 6.0mmol), pyridine (2.0mL, 25mmol) were added to a 25mL two-necked flask, and the oil bath was slowly heated to 100°C , after reflux stirring for 12h, TLC detects that raw material point 1 disappears;

[0026] In an ice-water bath environment, add 0.24g molecular sieves and methanol (2.9mL, 72mmol) to the two-necked flask, after proper stirring, slowly add thionyl chloride (1.5mL, 20mmol) dropwise, and remove the ice after about 1 hour. bath, stirring at room temperature for 16 hours;

[0027] Add 70-72% perchloric acid (1.6mL, 20mmol), acetonitrile (32mL) and deionized water (3.2mL) and stir the reaction for 0.5h, then gradually add saturated sodium bicarbonate to remove excess acid, and wait for the two-necked flask to Bubbles are generated again, stop stirring, filter to remove ...

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Abstract

The invention provides a one pot method for preparing aryl-alpha-keto ester based on arylethyl ketone, belonging to the technical field of organic chemical engineering. The method comprises the following steps: using arylethyl ketone as raw material to place in a reaction container, adding pyridine, piperidine or triethylamine used as solvent in the reaction container in turn, adding selenium dioxide to perform oxidation reaction and obtain aryl-keto acid, adding methanol and a defined amount of molecular sieve, placing the reaction container in ice bath, then dropwise adding thionyl chloridein the reaction container to perform esterification reaction, adding strong acid in the reaction container to perform hydrolysis reaction, then performing neutralization reaction and finally obtaining aryl-alpha-keto ester by washing, drying and filtrating. Compared with the prior art, the invention can greatly reduce the cost and simplify the operation while maintaining the yield; the raw materials can be obtained easily, the reaction yield is high, the synthesis cost is low and the yield can reach 80%.

Description

technical field [0001] The invention relates to a preparation method in the field of organic chemical technology, in particular to a one-pot preparation method of aryl α-ketoester based on aryl ethyl ketone. Background technique [0002] In the technical field of organic synthesis in the chemical industry, aryl α-ketoesters are important intermediates for the synthesis of various enzyme inhibitors and alkaloids. For example, as synthetic intermediates of fats, sugars, ribose, porphyrins, amino acids and proteins, as enzyme inhibitors or enzyme substrates, etc. At the same time, in recent years, aryl α-ketoesters have also been used in the synthesis of various compounds such as angiotensin transferase inhibitors, serine protease inhibitors, deoxyharringtonine, and homodeoxyharringtonine. Drugs synthesized from these compounds have certain curative effects on the treatment of hypertension, cancer and the like. Because of its importance in organic synthesis, enzyme inhibitors...

Claims

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Application Information

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IPC IPC(8): C07C69/738C07C67/08C07D307/54
Inventor 张万斌庄菁王常清谢芳
Owner SHANGHAI JIAO TONG UNIV
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