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Preparation method of substituted thiophene-3-one compound

A technology of ketone compounds and thiophene, which is applied in the field of preparation of substituted thiophene-3-ketone compounds, can solve the problems of poor environmental protection and high cost of raw materials, and achieve stable yields, increased total yields, and short synthetic routes.

Inactive Publication Date: 2018-05-29
ASYMCHEM LAB TIANJIN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The main purpose of the present invention is to provide a preparation method of substituted thiophene-3-one compounds, so as to solve the problems of high raw material cost and poor environmental protection in the existing preparation methods of substituted thiophene-3-one compounds

Method used

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  • Preparation method of substituted thiophene-3-one compound

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preparation example Construction

[0025] As described in the background art, the existing methods for preparing substituted thiophene-3-ones have the problems of high cost of raw materials and poor environmental protection. In order to solve the above technical problems, the invention provides a preparation method of substituted thiophene-3-one compounds, the preparation method comprising:

[0026] Michael addition reaction: Carry out Michael addition reaction between raw material A and raw material B to obtain the addition product, raw material A has the structure shown in formula (I), raw material B has the structure shown in formula (II), and the addition product has The structure shown in formula (Ⅲ),

[0027]

[0028] Among them, R 1 , R 2 , R 3 and R 4 independently selected from H, C 1 ~C 10 Alkyl or C 6 ~C 15 aryl; and

[0029] Dickman condensation reaction, the addition product is subjected to a Dickmann condensation reaction to obtain a substituted thiophene-3-one compound, and the substi...

Embodiment 1

[0052] FeCl 3 (1.625g, 0.01mol) was dissolved in acrylic acid (72g, 1mol) after being stirred and clarified, under nitrogen atmosphere, slowly added to thioglycolic acid (92g, 1mol) to obtain the system to be reacted;

[0053] Raise the temperature of the above-mentioned reaction system to 125 ° C, and stir for 1 h, sample HPLC, and obtain the addition product after the reaction of acrylic acid is completed;

[0054] The above-mentioned addition product system was heated up to 230° C. to carry out the Dickmann condensation reaction. After 1 hour, the reaction was completed, and the product system of the Dickmann condensation reaction was distilled to obtain 83 g of colorless liquid fraction and yellow liquid fraction product (tetrahydrothiophene-3 Ketone), the yield is 81wt%, and the purity is 95wt%.

[0055] The spectrogram data of the product are as follows:

[0056] 1 H NMR (500 MHz, DMSO) δ 3.23 (s, 2H), 3.01 (t, J = 7.1 Hz, 2H), 2.52 (t, J = 7.1 Hz, 2H).

[0057] EI-M...

Embodiment 2

[0059] The difference with Example 1 is: the catalyst is copper acetate.

[0060] After dissolving copper acetate (1.82g, 0.01mol) in acrylic acid (72g, 1mol) and stirring for clarification, under a nitrogen atmosphere, slowly add thioglycolic acid (92g, 1mol) to obtain a system to be reacted;

[0061] Raise the temperature of the above-mentioned reaction system to 125 ° C, and stir for 1 h, sample HPLC, and obtain the addition product after the reaction of acrylic acid is completed;

[0062] The above-mentioned addition product system was heated up to 230°C to carry out the Dickmann condensation reaction. After 1 hour, the reaction was completed, and the product system of the Dickmann condensation reaction was distilled to obtain a colorless distillate liquid and a yellow liquid distillate product (tetrahydrothiophene-3 ketone ), the yield of tetrahydrothiophene-3 ketone is 85wt%, and the purity is 97wt%.

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Abstract

The invention provides a preparation method of a substituted thiophene-3-one compound, comprising: subjecting material A and material B to Michael addition reaction to obtain an addition product; subjecting the addition product to Dieckmann condensation reaction to obtain a substituted thiophene-3-one compound having a structure shown as formula (IV) that is shown in the description. The preparation method provided by the application has the advantages that using solvents and strong bases is not required, reaction materials are low in price and easy to obtain, no wastewater is produce, and therefore, the preparation method has good environmental friendliness; compared with existing preparation methods, the preparation method has a short synthetic route, can be performed under mild conditions and features good yield stability and good repeatability, which is helpful for greatly increasing total yield of the substituted thiophene-3-one compound and helpful for industrial popularization.

Description

technical field [0001] The invention relates to organic synthesis, in particular to a method for preparing substituted thiophene-3-one compounds. Background technique [0002] Tetrahydrothiophene-3-one is a colorless to pale yellow liquid with an aroma of onion, garlic, meat, vegetables and cream. Tetrahydrothiophene-3-one is an important food flavor additive, and also a raw material for many active drug intermediates, such as ticarcillin sodium and thiopenem. Therefore tetrahydrothiophene-3-one is a chemical raw material with a wide range of applications and a large market demand. [0003] The synthetic route of Tetrahydrothiophene-3-one mainly contains: [0004] Existing literature discloses to obtain target product with 1-chloro-4-iodobutanone and sodium sulfide direct reaction ring closure condensation, the raw material cost of this method synthetic 1-chloro-4-iodobutanone is high, and reaction is complicated, difficult Large-scale production. [0005] Another docume...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/32
CPCC07D333/32
Inventor 卢江平张恩选刘志清张涛赵谦
Owner ASYMCHEM LAB TIANJIN
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