Preparation method of (carbethoxyethylidene)triphenylphosphorane

A technology of ethoxyformyl ethylene triphenylphosphine and triphenyl phosphine, which is applied in the field of preparation of ethoxyformyl ethylene triphenylphosphine, can solve the problem of pungent smell in the operating space and the increase of solvent Recovering costs, threatening human health and other issues, achieving the effects of shortening the production cycle, achieving continuity and high safety, and facilitating industrialized continuous production

Active Publication Date: 2014-07-09
ANHUI BIOCHEM BIO PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method mainly has the following disadvantages in industrialized large-scale production: 1) non-continuous operation, the middle needs to discharge, so that the total yield is reduced and the cost is increased; 2, in the process of centrifuge rejection and filtration to obtain quaternary phosphorus The liquid contains unreacted raw materials, causing a pungent smell in the operating space, which greatly threatens human health; 3) In the case of strong alkali treatment, a single or mixed organic solvent needs to be used, which increases the cost of solvent recovery

Method used

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  • Preparation method of (carbethoxyethylidene)triphenylphosphorane

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1 The preparation method of ethoxy formyl ethylene triphenylphosphine of the present invention

[0024] Add 131g of triphenylphosphine and 100g of ethyl 2-bromopropionate into a 1000mL three-neck flask, then add 200mL of toluene and 500ml of water, and stir at 80°C for 12h. After the reaction, cool to 50°C, separate the water layer, wash the water layer with 50ml of toluene, cool down to room temperature, add 10% sodium hydroxide solution dropwise to adjust the pH to 8.0-8.5, continue to stir for 1h, and filter to obtain the filter cake Dry at 50° C. to obtain 172 g of ethoxyformyl ethylene triphenylphosphine as a solid, with a yield of 95%.

[0025] The δ( 1 HNMR, DMSO-d 6 ): 7.40-7.80(m, 15H), 3.88(q, 0.92H, J=6.8Hz), 3.53(q, 1.18H, J=6.8Hz), 1.49(d, 3H, J=13.9Hz), 1.4 (t, 1.28H, J=6.8Hz), 0.38(t, 1.72H, J=6.8Hz) ppm. MS: 363 (MH + ).

Embodiment 2

[0026] Example 2 The preparation method of ethoxy formyl ethylene triphenylphosphine of the present invention

[0027] Add 131g of triphenylphosphine and 100g of ethyl 2-bromopropionate into a 1000mL three-neck flask, then add 200mL of toluene and 500ml of water, and stir at 80°C for 12h. After the reaction, cool to 50°C, separate the water layer, wash with 50ml of toluene, cool down to room temperature, add 10% potassium hydroxide solution dropwise to adjust the pH to 8.0-8.5, and continue stirring for 1h. After filtering, the resulting filter cake was dried at 50° C. to obtain 175 g of ethoxyformyl ethylene triphenylphosphine as a solid, with a yield of 96%.

[0028] The δ( 1 HNMR, DMSO-d 6 ): 7.40-7.80(m, 15H), 3.88(q, 0.92H, J=6.8Hz), 3.53(q, 1.18H, J=6.8Hz), 1.49(d, 3H, J=13.9Hz), 1.4 (t, 1.28H, J=6.8Hz), 0.38(t, 1.72H, J=6.8Hz) ppm. MS: 363 (MH + ).

Embodiment 3

[0029] Example 3 The preparation method of ethoxy formyl ethylene triphenylphosphine of the present invention

[0030] Add 131g of triphenylphosphine and 100g of ethyl 2-bromopropionate into a 1000mL three-neck flask, add 200mL of toluene and 500ml of water, and stir at 80°C for 12h. After the reaction, cool to 50°C, separate the water layer, wash with 50ml of toluene, cool down to room temperature, slowly add 20% sodium carbonate solution dropwise to adjust pH=8.0-8.5, continue to stir for 1h, filter, and the obtained filter cake is at 50°C Drying at a lower temperature yielded 160 g of ethoxyformyl ethylene triphenylphosphine as a solid, with a yield of 88%.

[0031] The δ(1HNMR, DMSO-d 6 ): 7.40-7.80(m, 15H), 3.88(q, 0.92H, J=6.8Hz), 3.53(q, 1.18H, J=6.8Hz), 1.49(d, 3H, J=13.9Hz), 1.4 (t, 1.28H, J=6.8Hz), 0.38(t, 1.72H, J=6.8Hz) ppm. MS: 363 (MH + ).

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Abstract

The invention relates to a preparation method of (carbethoxyethylidene)triphenylphosphorane. According to the method, after a reaction of triphenyl phosphine and ethyl 2-bromopropionate is completed in a solvent, the reaction products are not required to be separated, the pH value of a static separated water layer is directly regulated to 7.5-8.5, and the precipitate is collected to obtain the product. The method improves a two-step reaction of the prior art into a way that the intermediate products are not separated and a next-step reaction is directly carried out, simplifies the preparation steps, shortens the production cycle, and has the advantages of mild reaction conditions, simplified preparation steps, short production cycle, low manufacturing cost (reduced by about 40%), less three wastes, environmental protection, solvent recycling and reutilization, easily realized industrialized continuous production and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of ethoxyformyl ethylene triphenylphosphine. Background technique [0002] The Witting reaction refers to the reaction of a Witting reagent with a carbonyl compound to form an alkene, and is named after the German chemist who first discovered the reaction. The reaction yield is high, the reaction conditions are mild, and it has high position selectivity. [0003] Witting reagent is phosphorus ylide, which is usually obtained by reacting tertiary phosphorus with halogenated hydrocarbons, and then treated with strong alkali. Among them, ethoxyformyl ethylene triphenylphosphine (structure shown in formula I) is an effective Witting reagent. At present, there are few reports on the preparation method of ethoxyformyl ethylene triphenylphosphine. The traditional method for synthesizing phosphorus ylides comprises the following steps: 1) usi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/535
Inventor 岳祥军钟晓锋王志邦
Owner ANHUI BIOCHEM BIO PHARMA
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