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Bis(methylsiloxy)ferrocene tricarbon ester monomer and preparation method thereof

A technology of bismethylsiloxytricarbonate ferrocene and siloxytricarbonate ferrocene is applied in the field of preparation of bismethylsiloxytricarbonate ferrocene monomer, which can solve the problem of expensive raw materials , Harsh preparation conditions, limited sources of raw materials, etc., to achieve the effect of wide source of raw materials, simple and easy preparation, and low price of raw materials

Inactive Publication Date: 2015-10-07
SUZHOU CINC TEXTILE TECH RP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The earliest method was to acylate ferrocene by Friedel-Crafts, or acetyl ferrocene was catalyzed by NaNH2, respectively, to prepare carbonyl-containing three-carbon ferrocene ester, and further PtO2 Catalyzed decarbonylation to obtain ester group-containing three-carbon ferrocene. Obviously, this method has limited sources of raw materials, harsh preparation conditions, and low double substitution yield, which makes it only suitable for small-scale preparation in the laboratory; the most recent typical The Witt ig-Horner reaction synthesis route has opened up the preparation of three-carbon esters, but this route has the problem of expensive raw materials and the need for catalytic hydrogenation of noble metal catalysts

Method used

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  • Bis(methylsiloxy)ferrocene tricarbon ester monomer and preparation method thereof
  • Bis(methylsiloxy)ferrocene tricarbon ester monomer and preparation method thereof
  • Bis(methylsiloxy)ferrocene tricarbon ester monomer and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0024] Dissolve 6.684 g of dialdehyde ferrocene (27.6 mmol) and 11.8 mL of 1-methoxy-1-(trimethylsilyloxy)-2-methyl-1-propene (55.3 mmol) in 100.0 mL of anhydrous dichloromethane ) in the dry Schlenk bottle of 250mL, under the protection of dry nitrogen, quickly drop 0.768g MgI 2 (2.8mmol) in 50.0mL ether solution, after stirring at room temperature for 6.0 hours, 10.0mL saturated NaHCO was added dropwise 3 Quenched, separated to obtain the bottom organic layer, removed the volatile solvent and dried in vacuo, further used 200 mesh to 300 mesh silica gel as the carrier, and used petroleum ether and ethyl acetate as the eluent to obtain the first fraction 5.929g 1 , 1'-bis(2-methoxycarbonyl-2-methyl-1-trimethylsilyloxy-propyl)ferrocene, the yield was 38.3%. Its chemical structure is:

[0025]

[0026] see attached figure 1 , which are respectively the compound (1,1'-bis(2-methoxycarbonyl-2-methyl-1-trimethylsilyloxy-propyl)ferrocene) prepared in this example 13 C NMR ...

Embodiment 2

[0029] Dissolve 6.873 g of dialdehyde ferrocene (28.4 mmol) and 18.2 mL of 1-methoxy-1-(trimethylsilyloxy)-2-methyl-1-propene (85.2 mmol) in 100.0 mL of anhydrous dichloromethane ) in the dry Schlenk bottle of 250mL, under the protection of dry nitrogen, add 1.580g MgI dropwise rapidly 2 (5.7mmol) in 50.0mL ether solution, after stirring at room temperature for 6.0 hours, 10.0mL saturated NaHCO was added dropwise 3 Quenched, separated to obtain the bottom organic layer, removed the volatile solvent and dried in vacuum, further used 200-300-mesh silica gel as a carrier, and used petroleum ether and ethyl acetate as eluents for gradient elution to obtain the first fraction 7.060g 1 , 1'-bis(2-methoxycarbonyl-2-methyl-1-trimethylsilyloxy-propyl)ferrocene, the yield was 42.1%.

[0030] Compound (1,1'-bis(2-methoxycarbonyl-2-methyl-1-trimethylsilyloxy-propyl)ferrocene) prepared in this example 1 H NMR spectrum (400MHz, CDCl 3 ,ppm) and 13 C NMR spectrum (300MHz, CDCl 3 , ppm) ...

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Abstract

The invention relates to a bis(methylsiloxy)ferrocene tricarbon ester monomer and a preparation method thereof. The chemical structural formula of the bis(methylsiloxy)ferrocene tricarbon ester monomer is shown in a formula I as described in the specification. The preparation method for the monomer comprises a step of reacting 1,1'-ferrocenedialdehyde with 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propylene under the catalysis of a catalyst--magnesium iodide diethyl ether complex. The bis(methylsiloxy)ferrocene tricarbon ester monomer prepared in the invention can be used for preparation of a conductive material.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to a bismethylsiloxy tricarbonate ferrocene monomer and a preparation method for a bismethylsiloxy tricarbon ester ferrocene monomer. Background technique [0002] Ferrocene derivatives have unique optical and electrical properties and are widely used in industrial manufacturing. On the one hand, due to the existence of ferrocene in the structure, it has obvious absorption characteristics of ultraviolet-visible light; on the other hand, through the modification of some polymerizable groups, polymer materials containing ferrocene can be prepared. These iron-containing hybrid Polymer materials have been widely studied and applied in the field of functional materials. Scientific researchers focus on the synthesis of various polymerizable ferrocene derivatives, mainly including chain polymerizable monomers and stepwise polymerizable monomers. Among them, the commercial products of...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 黄志向王建军翟涛邱殿銮杨金虎戴礼兴
Owner SUZHOU CINC TEXTILE TECH RP
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