Method for preparing 4-bialkoxy-phosphono-2-methyl-2-butenoic acid alkyl ester

A technology of dihydrocarbyloxyphosphono and crotonate hydrocarbyl esters, which is applied in the fields of chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., and can solve problems such as suboptimal methods, heavy pollution, Process complexity and other issues

Active Publication Date: 2013-05-22
广州巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] This method has the following disadvantages: 4-halogenated tiglate (4-halotiglate) is not a directly available basic chemical raw material, the process for preparing it is complicated, the pollution is large, or the raw material is not easy to obtain
[0016] In summary, there are fewer methods for preparing 4-dihydrocarbyloxyphosphono-2-methyl-2-butenoic acid alkyl esters at present, and none of them are preferred methods. Therefore, research on the preparation of 4-dihydrocarbyloxy Other preparation methods of phosphono-2-methyl-2-butenoic acid alkyl ester are necessary

Method used

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  • Method for preparing 4-bialkoxy-phosphono-2-methyl-2-butenoic acid alkyl ester
  • Method for preparing 4-bialkoxy-phosphono-2-methyl-2-butenoic acid alkyl ester
  • Method for preparing 4-bialkoxy-phosphono-2-methyl-2-butenoic acid alkyl ester

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Dissolve 41.0g (0.22mol) diethyl 2-oxoethylphosphate and 80.0g (0.22mol) ethyl 2-triphenylphosphine ylide propionate in 400ml dichloromethane under nitrogen protection and 25°C , stirred and heated to 40° C. for reflux reaction for 20 hours. After the reaction was completed, dichloromethane was removed by concentration under reduced pressure, 200ml of n-heptane was added and the temperature was lowered to 0°C to precipitate triphenylphosphine oxide crystals, which were removed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent to obtain 67.9 g of a yellow oil, mainly 4-diethoxyphosphono-2-methyl-2-butenoic acid ethyl ester, which was purified by a silica gel column to obtain 51.0 g of the product, Yield 88%.

Embodiment 2

[0037]Under nitrogen protection and 25°C, dissolve 41.0g (0.22mol) of 2-oxoethyl diethyl phosphate in 100ml of dichloromethane, then add 80.0g (0.22mol) of 2-triphenylphosphine dropwise under stirring A solution of ethyl ylide propionate dissolved in 400 ml of dichloromethane took about 120 minutes. After the dropwise addition was completed, the temperature was raised to 40° C. for reflux reaction for 10 hours. After the reaction was completed, dichloromethane was removed by concentration under reduced pressure, 200ml of n-heptane was added and the temperature was lowered to 0°C to precipitate triphenylphosphine oxide crystals, which were removed by filtration. The filtrate was concentrated under reduced pressure to obtain 66.2g of yellow oil, mainly 4-diethoxyphosphono-2-methyl-2-butenoic acid ethyl ester, purified by silica gel column to obtain 48.8g of product, the yield 84%.

Embodiment 3

[0039] Dissolve 34.5g (0.22mol) dimethyl 2-oxoethylphosphate and 80.0g (0.22mol) ethyl 2-triphenylphosphine ylide propionate in 400ml dichloromethane under nitrogen protection and 25°C , reflux reaction for 20 hours. After the reaction was completed, dichloromethane was removed by concentration under reduced pressure, 200ml of n-heptane was added and the temperature was lowered to 0°C to precipitate triphenylphosphine oxide crystals, which were removed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent to obtain 64.2 g of a yellow oil, mainly 4-dimethoxyphosphono-2-methyl-2-butenoic acid ethyl ester, which was purified by a silica gel column to obtain 44.6 g of the product, Yield 86%.

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Abstract

The invention discloses a method for preparing 4-bialkoxy-phosphono-2-methyl-2-butenoic acid alkyl ester. According to the method, a compound shown in a formula A and a compound shown in a formula B have reaction to generate a compound having a general formula I. The method has the advantages that raw materials are easily available sources, reaction is stable and reliable, reaction conditions are mild, and environment-friendliness effect is achieved, and the method is very suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing 4-dihydrocarbyloxyphosphono-2-methyl-2-butenoic acid hydrocarbyl ester. Background technique [0002] 4-dihydrocarbyloxyphosphono-2-methyl-2-butenoic acid alkyl ester (general formula I) is mainly used in the field of polyene chemistry, especially carotenoids, for the preparation of conjugated polyene carboxylic acids and their derivatives substances, such as diethyl crocinate, β-apo-8'-ethyl carotate and β-apo-4'-ethyl carotate, etc. [G.Britton, S.Liaaen-jensen, H.Pfander , Carotenoids Volume 2: Synthesis. Verlag, Basel and Boston, Berlin. 1996, 279-280; W. Dobler, W. Krause and J. Paust, et al., BASF, US. Pat. 5773635, 1998; H. Ernst, K. Henrich, US. Pat.158472,2003 and G.Pattenden and B.C.L.Weedon,J.Chem.Soc.(C),1968,1997-2006, etc.]; in addition, it is also used as a bifunctional intermediate in other polyene chemistry, for example, Construction of conjugated polyene chains [X.Liu and G.D.Prestwic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/6574
Inventor 关裕时韦铧洪姚伟平廖艳金刘庆辉
Owner 广州巨元生化有限公司
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