Method of preparing r-butenolide from alkenyl epoxide

A technology of butenolide and oxygen compound, applied in the direction of organic chemistry, etc., can solve the problem of few r-butenolide methods, and achieve the effects of condition optimization, high atom utilization rate, and low environmental hazards

Inactive Publication Date: 2017-03-15
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The method of synthesizing butene lactone has been reported in a large number, but normal temperature, does not use metal catalyst, the method for fast and efficient synthesis r-butene lactone is still less, especially simple operation, one-step synthesis alkenyl substituted butene lactone Methods for ester compounds are less reported

Method used

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  • Method of preparing r-butenolide from alkenyl epoxide
  • Method of preparing r-butenolide from alkenyl epoxide
  • Method of preparing r-butenolide from alkenyl epoxide

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Experimental program
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Effect test

Embodiment 1

[0032] Add 0.5mL of dichloromethane to the reaction flask, then add 10.2mg (0.05mmol) of alkenyl epoxy compound, 17.4mg (0.1mmol) of trifluoroacetophenone, stir for a few minutes, and then add 12.4 ul (0.05 mmol) of tributylphosphine, stirred vigorously at room temperature, monitored by TLC, after the reaction was completed, separated the product by thin layer chromatography (petroleum ether: ethyl acetate = 6:1), and obtained 14.5 mg of the corresponding product , and the yield was 88%.

Embodiment 2

[0034] Add 0.5mL of dichloromethane to the reaction flask, then add 10.2mg (0.05mmol) of alkenyl epoxy compound, 10.1ul (0.1mmol) of benzaldehyde, stir for a few minutes, then add 12.4ul (0.05 mmol) of tributylphosphine, vigorously stirred at room temperature, monitored by TLC, after the reaction was completed, the product was separated by thin-layer chromatography (petroleum ether: ethyl acetate=6:1), and 8.0 mg of the corresponding product was obtained. was 61%.

Embodiment 3

[0036] Add 0.5mL of dichloromethane to the reaction flask, then add 10.2mg (0.05mmol) of alkenyl epoxy compound, 8.7ul (0.1mmol) of morpholine, 6.9ul (0.05mmol) of triethylamine, at room temperature Vigorously stirred and monitored by TLC. After the reaction was completed, the product was separated by thin layer chromatography (petroleum ether: ethyl acetate = 4:1) to obtain 11.5 mg of the corresponding product with a yield of 89%.

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Abstract

The invention discloses a method of preparing r-butenolide from alkenyl epoxide. The method includes taking the MBH type alkenyl epoxide as a raw material, and allowing a reaction between the MBH type alkenyl epoxide and nucleophile to obtain the r-butenolide at the room temperature. The method has the advantages of mild reaction condition, non-use of metal catalysts, and high efficiency and speed under room temperature.

Description

technical field [0001] The invention relates to the field of pharmaceutical chemical synthesis, in particular to a method for preparing r-butenolide by using alkenyl epoxy compounds. Background technique [0002] The synthesis of γ-butyrolactone structure has very important pharmaceutical application value, it not only widely exists in natural products and a variety of biologically active molecules, such as steroidal cardiac glycosides digoxin (1), vitamin C (2), anticancer active annonaceous lactone compounds, etc., are also the structural units of an important synthetic COX selective inhibitor class anti-inflammatory and analgesic drug rofecoxib (3), so effectively synthesize γ- The structure of butyrolactone has always been an important research direction in synthetic methodology and natural product synthesis chemistry. [0003] [0004] The method of synthesizing butenolactone has been reported in a large number, but normal temperature, do not use metal catalyst, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 肖华袁哲哲马娟孔祥文姚日升刘丽华
Owner HEFEI UNIV OF TECH
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