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Preparation method of 4-alkyl-5-alkoxy oxazole compound

An alkoxyoxazole and compound technology, applied in the field of organic synthesis, can solve problems such as difficult transesterification, and achieve the effects of convenient industrial production, high yield and low production cost

Active Publication Date: 2020-01-21
SHANDONG NHU FINE CHEM SCI & TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, those skilled in the art generally believe that the carbonyl group in the oxazole ester compound is conjugated to the oxazole ring, so the ester group is very stable, and it is difficult to efficiently transesterify. At present, there is no relevant method to report the transesterification reaction of the oxazole ester compound.

Method used

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  • Preparation method of 4-alkyl-5-alkoxy oxazole compound
  • Preparation method of 4-alkyl-5-alkoxy oxazole compound
  • Preparation method of 4-alkyl-5-alkoxy oxazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] In the reaction flask, add 19.92g of ethyl 4-methyl-5-ethoxyxazolecarboxylate (0.1mol) and 8.58mL of acetic acid (0.15mol), then add 20mL of acetonitrile, and stir at 70°C for 2 hours. Treat that system does not have bubble to emerge, and reaction finishes, and the internal standard yield of gas chromatography detection product is 68.5% (n-dodecane is internal standard), generates 1.3% N-formylalanine ethyl ester simultaneously (area normalized Law).

Embodiment 2

[0036] In the reaction flask, add 19.92g ethyl 4-methyl-5-ethoxy oxazolecarboxylate (0.1mol), 8.58mL acetic acid (0.15mol) and 0.37mL trifluoroacetic acid (0.005mol), then add 20mL Acetonitrile, stirred at 70°C for 2 hours. Treat that system does not have bubble to emerge, and reaction finishes, and the internal standard yield of gas chromatography detection product is 98.5% (n-dodecane is internal standard), generates 0.6% N-formylalanine ethyl ester simultaneously (area normalized Law). Ten batches of the resulting reaction solution were collected and rectified under reduced pressure to obtain 122.32 g of a qualified product with a yield of 96.21%.

[0037] The product is characterized, and the obtained hydrogen spectrum is as follows figure 1 As shown, the obtained carbon spectrum is as figure 2 shown.

Embodiment 3

[0039] In the reaction flask, add 19.92g ethyl 4-methyl-5-ethoxyoxazolecarboxylate (0.1mol), 6.86mL acetic acid (0.12mol) and 0.37mL trifluoroacetic acid (0.005mol), then add 20mL Acetonitrile, stirred at 70°C for 2 hours. Treat that system does not have bubble to emerge, and reaction finishes, and the internal standard yield of gas chromatography detection product is 91.2% (n-dodecane is internal standard), generates 0.1% N-formylalanine ethyl ester simultaneously (area normalized Law).

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Abstract

The invention discloses a preparation method of a 4-alkyl-5-alkoxy oxazole compound. The preparation method comprises the following steps: under the action of a catalyst, carrying out transesterification on 4-alkyl-5-alkoxy oxazole-2-carboxylic ester and acid in a solvent to obtain an oxazole acid intermediate, and carrying out decarboxylation reaction on the oxazole acid intermediate to obtain the 4-alkyl-5-alkoxy oxazole compound. The preparation method has the advantages of no wastewater generation in the reaction process, cheap and accessible catalyst and high reaction yield, and is convenient for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of 4-alkyl-5-alkoxy-oxazole compounds. Background technique [0002] Esters are an important class of organic compounds. Among them, the deesterification reaction of ester is used for VB6 synthesis [Selected papers: (a) Maeda, I.; Takehara, M.; Togo, K.; Asai, S.; Bull.Chem.Soc.Japan.1969,42, 1435-1437; (b) Zou, Y.; Shi, X.J.; Li, Z.H.; Jin, C.; The traditional deesterification reaction includes three steps of saponification, acidification and decarboxylation. A large amount of waste water is produced in the process of saponification and acidification, and the yield is not high, which increases the cost of industrial production. [0003] Chinese patent applications whose publication numbers are CN 109305946 A, CN 104447605 A, and CN 102321043 A disclose a synthetic method for 4-methyl-5-ethoxy oxazole, which includes 4-alkyl-5- The three steps of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/42
CPCC07D263/42
Inventor 陈卫勇赵雷黄尖王海涛盛美兰吴元元吴旭东梁昊苏伟伟
Owner SHANDONG NHU FINE CHEM SCI & TECH CO LTD