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Method for synthesizing 4-vinyl-2(5H)-furanone

A synthetic method and vinyl technology, applied in the direction of organic chemistry, can solve the problems of expensive price, expensive reagents, and inability to scale up production, and achieve the effect of solving mass production problems, simple and convenient separation and purification, and low toxicity of reagents

Inactive Publication Date: 2019-08-27
SHENZHEN ELDERLY MEDICAL RES INST +1
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0010] At present, the synthesis of 4-vinyl-2(5H)-furanone reported in the literature is very inefficient, and there are many shortcomings such as low yield, complex operation, expensive reagents, and inability to scale up production. Therefore, 4-vinyl- The price of 2(5H)-furanone is also relatively expensive (1g / $1760, Accel Pharmtech Company), which also limits the use of 4-vinyl-2(5H)-furanone, a highly active organic intermediate, in drug synthesis, etc. Aspects of application

Method used

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  • Method for synthesizing 4-vinyl-2(5H)-furanone

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Embodiment

[0024] The synthetic method of 4-vinyl-2(5H)-furanone

[0025]

[0026] (1) Add 250mL of methanol to a 500mL three-necked flask, add 5g of sodium metal at 0°C, and slowly add 24mL of thiophenol (PhSH) dropwise after the Na is completely dissolved, stir at 0°C for 20 minutes, and then add α-bromo - 29g of γ-butyrolactone (compound 9), stirred at room temperature for 2 hours, quenched the reaction by adding water, then extracted with acetic acid, the extract was dried and concentrated, and the concentrated product was separated by silica gel column chromatography to obtain α-phenylthio-γ- Butyrolactone (compound 10) 26g, the reaction yield is 77%.

[0027] The NMR identification results of α-phenylthio-γ-butyrolactone are: 1 H NMR (CDCl 3 ,300MHz)δ2.28 (ddd,J=6.2,10.4,15.7Hz,1H),2.63-2.72(m,1H),3.84-3.88(m,1H),4.19-4.27(m,2H),7.34- 7.35 (m, 3H), 7.55-7.57 (m, 2H).

[0028] (2) 9.3 g of α-phenylthio-γ-butyrolactone (compound 10) and 9.8 g of m-chloroperoxybenzoic acid (m-C...

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Abstract

The invention discloses a method for synthesizing 4-vinyl-2(5H)-furanone. The method comprises the following steps: step (1) taking and adding metal sodium into methanol, dripping thiophenol into themethanol, and then continuously adding alpha-bromo-gamma-butyrolactone for reaction to obtain alpha-phenylthio-gamma-butyrolactone; step (2) taking alpha-phenylthio-gamma-butyrolactone and m-chloroperoxybenzoic acid to react at 0 DEG C, and then adding trifluoroacetic anhydride for continuing reaction to obtain alpha-phenylthio-gamma-butenolactone; step (3) taking alpha-phenylthio-gamma-butenolactone, vinyl magnesium bromide and copper (I) bromide-dimethyl sulfide to react at -78 DEG C to obtain 3-phenylthio-4-vinyl-gamma-butyrolactone; step (4) taking 3-phenylthio-4-vinyl-gamma-butyrolactoneand m-chloroperoxybenzoic acid to react at 0 DEG C, and then adding toluene for continuing reaction at 120 DEG C to obtain 4-vinyl-2(5H)-furanone. The method provided by the invention has advantages of high total yield, low cost and simplicity in separation and purification.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a synthesis method of 4-vinyl-2(5H)-furanone. Background technique [0002] 4-Vinyl-2(5H)-furanone is a five-membered lactone containing a conjugated double bond. It has good reactivity and is a highly active, multi-reactive organic synthesis intermediate. The intermediate can carry out various forms of Michael addition reactions and tandem ring-forming reactions. Therefore, this intermediate has a wide range of uses in the field of basic research in organic synthesis or in the development of medicinal chemistry and even the pharmaceutical industry, and has good development value. . [0003] In 1974, the Mori research group reported the synthesis of compound 3. Starting from compound 2, compound 3 was obtained through Johnson-Claisen rearrangement; then compound 4 was obtained by connecting a phenylthio group at the alpha position of the ester group, and then oxidized...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 陶成吴正治刘展艳李利民
Owner SHENZHEN ELDERLY MEDICAL RES INST
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