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A kind of synthetic method of trialkyl (alpha-alkoxyethylene) tin

A technology of alkoxyethylene and alkoxyvinyl ether, which is applied in the synthesis field of trialkyltin, can solve the problems of inability to produce intermediates on a large scale, limit large-scale application, and high cost of catalysts, reduce energy consumption, The effect of reducing risk and improving safety

Active Publication Date: 2018-07-17
无锡贝塔医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, the ethoxytributyltinacetylene used is also an intermediate that cannot be produced on a large scale, and the cost of the Ru catalyst is also high, which limits the large-scale application of this method

Method used

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  • A kind of synthetic method of trialkyl (alpha-alkoxyethylene) tin
  • A kind of synthetic method of trialkyl (alpha-alkoxyethylene) tin
  • A kind of synthetic method of trialkyl (alpha-alkoxyethylene) tin

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Experimental program
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Effect test

Embodiment 1

[0033] Embodiment 1: following formula ( ) The preparation of tributyl (α-ethoxyethylene) tin

[0034]

[0035] Under nitrogen protection, 112g potassium tert-butoxide (1mol) and 139.2g tetramethylethylenediamine (1.2mol) were added to 1000ml n-hexane, cooled to -30°C; Lithium n-hexane solution 400ml, added dropwise in 1.5 hours, reacted at this temperature for 0.5 hours, then cooled to -40°C; dissolved 108g vinyl ether (1.5mol) in 200ml anhydrous tetrahydrofuran, added dropwise to the above mixed solution Keep at -40°C, add about 0.5 hours, heat up to -20°C for 1 hour, then cool down to -78°C; dissolve 227.9g of tributyltin chloride (0.7mol) in 500ml of anhydrous tetrahydrofuran Add dropwise to the above mixed solution, keep at -78°C, dropwise is completed in about 2 hours, naturally warm up and stir for 8 hours; slowly add 400ml of saturated ammonium chloride dropwise under ice bath to quench, filter, and separate the filtrate. Collect the organic phase, extract the aq...

Embodiment 2

[0037] Embodiment 2: following formula ( ) The preparation of trimethyl (α-methoxyethylene) tin

[0038]

[0039] Under the protection of nitrogen, 98g potassium isopropoxide (1mol) and 168g tetramethylethylenediamine (1.5mol) were added to 1300ml n-hexane, and the temperature was lowered to -40°C; Lithium n-hexane solution 480ml, added dropwise in 2 hours, reacted at this temperature for 1 hour, then cooled to -50°C; dissolved 69.6g vinyl methyl ether (1.2mol) in 150ml anhydrous tetrahydrofuran, added dropwise to the above Remove from the mixed solution, keep at -50°C, add in 1 hour, raise the temperature to -30°C for 1 hour, then cool down to -78°C; dissolve 159.2g of trimethyltin chloride (0.8mol) in 400ml of anhydrous In tetrahydrofuran, add dropwise to the above mixed solution, keep at -78°C, add dropwise for about 2 hours, naturally raise the temperature and stir for 8 hours; slowly add 450ml saturated ammonium chloride dropwise under ice bath to quench, filter, and...

Embodiment 3

[0041] Embodiment 3: following formula ( ) The preparation of tributyl (α-methoxyethylene) tin

[0042]

[0043] Under nitrogen protection, add 84g of potassium ethylate (1mol) and 232g of tetramethylethylenediamine (2mol) into 1600ml of n-hexane, cool down to -40°C; add dropwise n-hexane with a molar concentration of 2.5 n-butyllithium The solution was 500ml, and the dropwise addition was completed in 2 hours, reacted at this temperature for 1 hour, and then cooled to -50°C; dissolved 104.4g of vinyl methyl ether (1.8mol) in 300ml of anhydrous tetrahydrofuran, and added dropwise to the above mixed solution. , keep at -50°C, add about 1 hour, raise the temperature to -30°C for 1 hour, then cool down to -78°C; dissolve 260.4g of trimethyltin chloride (0.8mol) in 500ml of anhydrous tetrahydrofuran, Add it dropwise to the above mixed solution, keep it at -78°C, finish the dropwise addition in about 2 hours, raise the temperature naturally and stir for 8 hours; slowly add 500...

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Abstract

The invention relates to a trialkyl(alpha-alkoxy ethylene)tin synthesis method. The method is characterized by including: dissolving a fatty alcohol alkali metal compound and tetramethylethylenediamine into n-hexane under nitrogen protection, dropwise adding n-hexane solution of n-butyllithium, dissolving alpha-alkoxy vinyl ether into anhydrous tetrahydrofuran, dropwise adding into mixed solution, and cooling to -78 DEG C; dissolving trialkyl tin chloride in anhydrous tetrahydrofuran, dropwise adding into mixed solution at the same temperature, performing TLC test reaction, adding saturated ammonium chloride aqueous solution for quenching reaction under an ice bath condition after TLC test reaction is finished, filtering the solution, separating filtrate, collecting organic phases, combining the organic phases, sequentially washing the organic phases with water and saline solution, filtering, concentrating and drying to obtain crude products of trialkyl(alpha-alkoxy ethylene)tin. The trialkyl(alpha-alkoxy ethylene)tin synthesis method has advantages of safety, convenience and massive cost reduction.

Description

technical field [0001] The invention relates to a synthesis method of trialkyl (α-alkoxyethylene) tin, belonging to the field of organic synthesis chemistry. Background technique [0002] The stille coupling reaction catalyzed by transition metal palladium has become a very effective way to construct carbon-carbon bonds. It has high selectivity, strong compatibility with substrates, and can allow the existence of various functional groups in substrates. In addition, the product of this reaction is a salt, which is relatively easy to isolate. Therefore, the Stille coupling reaction has been more and more widely used in material synthesis, drug synthesis and total synthesis of complex natural products. [0003] Trialkyl(α-alkoxyethylene)tin is an important organotin reagent in the Stille coupling reaction, for example, tributyl(α-ethoxyethylene)tin is an efficient palladium-catalyzed halogenation (MasanoriKOSUGI*, Takashi SUMIYA, et al. (α-Ethoxyvinyl)tributyltin: An Efficie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/22
CPCC07F7/2208
Inventor 王玮费静李刚
Owner 无锡贝塔医药科技有限公司