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Tetrahydrofuran ring-opening double-silylation reaction method

A tetrahydrofuran, silylation technology, applied in chemical instruments and methods, silicon-organic compounds, organic chemistry, etc., can solve the problems of severe reaction conditions, long reaction time, low yield, etc., and achieves simple operation, low cost, and high yield. high rate effect

Active Publication Date: 2021-08-24
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although this reaction selectively obtains tetrahydrofuran ring-opening disilylation products, the reaction conditions are severe, the reaction time is long, and the yield is low.

Method used

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  • Tetrahydrofuran ring-opening double-silylation reaction method
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  • Tetrahydrofuran ring-opening double-silylation reaction method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Ring-opening trimethylsilylation reaction of tetrahydrofuran under the condition of no catalyst and additives.

[0023] The reaction formula is as follows:

[0024]

[0025] The reaction steps are as follows: In a glove box, add Mg powder (7.9mmol, 192mg), THF (7.9mmol, 0.64mL), TMSCl (7.9mmol, 1mL) to a 4mL reaction vessel equipped with magnetons, seal and transfer After stirring and reacting at 60° C. for 24 h, dilute with DCM and transfer to a 100 mL round-bottomed flask to obtain a reaction solution containing the intermediate product P. Calculate the yield of the intermediate product P. The measuring method of the yield of the intermediate product P is as follows: 1) First prepare a mixture of the standard product intermediate P and the internal standard sample dodecane with a certain molar gradient for gas chromatography analysis, measure the peak area, and obtain the relationship curve between the peak area ratio and the molar ratio of P and the int...

Embodiment 2

[0026] Example 2: Ring-opening trimethylsilylation reaction of tetrahydrofuran under the catalyst condition of samarium iodide.

[0027] The reaction formula is as follows:

[0028]

[0029] The reaction steps are as follows: In the glove box, add SmI to a 4mL reaction vessel equipped with a magnet 2 (0.064mmol) in THF (0.64mL), Mg powder (7.9mmol, 192mg), TMSCl (7.9mmol, 1mL), sealed, transferred to 60°C and stirred for 24h, then diluted with DCM and transferred to a 100mL round bottom flask , Promptly get the reaction solution that contains intermediate product P, calculate the productive rate of intermediate product P, the measuring method of the productive rate of intermediate product P is as follows: 1) prepare the standard product intermediate product P of certain molar weight gradient and internal standard sample twelve The mixture of alkane is analyzed by gas chromatography, the peak area is measured, and the relationship curve between P and the internal standard p...

Embodiment 3

[0030] Example 3: Ring-opening trimethylsilylation reaction of tetrahydrofuran under the catalyst condition of samarium iodide.

[0031] The reaction formula is as follows:

[0032]

[0033] The reaction steps are as follows: In the glove box, add SmI to a 4mL reaction vessel equipped with a magnet 2 (0.064mmol) in THF (0.64mL), Mg powder (15.8mmol, 384mg), TMSCl (7.9mmol, 1mL), sealed and transferred to 40°C for 24h, then diluted with DCM and transferred to a 100mL round bottom flask , Promptly get the reaction solution that contains intermediate product P, calculate the productive rate of intermediate product P, the measuring method of the productive rate of intermediate product P is as follows: 1) prepare the standard product intermediate product P of certain molar weight gradient and internal standard sample twelve The mixture of alkane is analyzed by gas chromatography, the peak area is measured, and the relationship curve between P and the internal standard peak area...

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Abstract

The invention provides a tetrahydrofuran ring-opening double-silylation reaction method, and the reaction formula of the tetrahydrofuran ring-opening double-silylation reaction is shown in the specification, in the formula, R1, R2 and R3 are respectively and independently selected from methyl, ethyl and isopropyl; a catalyst used in the tetrahydrofuran ring-opening double-silylation reaction is SmI2, NaI, KI or ZnI2. According to the tetrahydrofuran ring-opening double-silylation reaction method, samarium iodide is used as a catalyst, the reaction condition is mild, and the yield is high; in addition, the method for preparing the double-silicon-based target product through one-step tetrahydrofuran ring opening is simple in operation; in addition, use of active alkali metal is avoided, cheap and easily available raw materials and catalyst are used, and the cost is low; furthermore, the catalyst samarium iodide and the tris (pentafluorophenyl) borane can generate a synergistic effect, and a 1 + 1 > 2 promoting effect is generated on the tetrahydrofuran ring-opening double-silylation reaction.

Description

technical field [0001] The patent of the present invention relates to the field of organic synthesis, especially to the preparation method of alkyl silicon organic compounds. Background technique [0002] The ring-opening functionalization reaction of tetrahydrofuran is an effective way to synthesize n-butane substituted by terminal difunctional groups (Progress in Heterocyclic Chemistry, 2009, 20, 152; Inorg.Chem.2004, 43, 4427; J.Am.Chem.Soc.2007, 129, 1246; Dalton Trans. 2013, 42, 695; Polyhedron 2013, 65, 308; J. Chin. Chem. Soc. 2015, 62, 703;). Wherein, tetrahydrofuran reacts with chlorosilane to obtain terminal functionalized siloxy-protected butane derivatives. At high temperature (130° C.), trimethylchlorosilane can make tetrahydrofuran ring-opening reaction to generate siloxybutyl chloride, but the reaction yield is low (12h, 58%) (Russ.Chem.Bull., Int. Ed. 2018, 67, 1621). [0003] In the presence of excess sodium iodide, the corresponding siloxybutyl chloride ...

Claims

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Application Information

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IPC IPC(8): C07F7/08
CPCC07F7/081C07F7/0827Y02P20/584
Inventor 张敬裴娜罗欢欢
Owner WUHAN UNIV
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