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Synthetic method of asymmetrical ether by gold-catalysis

A synthetic method and asymmetric technology, applied in the field of synthesis of gold-catalyzed asymmetric ethers, achieving good yield, high product purity, and mild reaction conditions

Inactive Publication Date: 2015-02-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, there is no such a method of directly dehydrating between two alcohol molecules to obtain an asymmetric ether

Method used

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  • Synthetic method of asymmetrical ether by gold-catalysis
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  • Synthetic method of asymmetrical ether by gold-catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Phenethyl alcohol (0.5 mmol, 61.2 mg) and benzyl alcohol (1.5 mmol, 162.1 mg) were added to a 10 mL microwave tube, and Ph 3 PAuCl (0.00025mmol, 0.2mg), the reaction mixture was heated to 150° C. with a microwave reactor, stirred for 90 minutes, and after completion of the reaction, the target product I was isolated by flash column chromatography with a yield of 96%.

[0031] The reaction formula of benzyl alcohol and phenethyl alcohol is:

[0032]

[0033] The spectral data of product I are: ESI-MS (m / z): 213 [M+H] + ; 1 H-NMR (600MHz, CDCl 3 )δ7.41-7.44(m,5H),7.34-7.38(m,3H),7.26-7.30(m,2H),4.58(s,2H),3.76(t,J=7.2Hz,2H),3.00 (t,J=7.2Hz,2H).

Embodiment 2

[0035] Using cyclohexanol instead of phenethyl alcohol, the other is the same as in Example 1, to obtain the target compound II with a yield of 76%. The reaction formula of benzyl alcohol and cyclohexanol is:

[0036]

[0037] The spectral data of product II are: ESI-MS (m / z): 191 [M+H] + ; 1 H-NMR (600MHz, CDCl 3)δ7.32–7.38(m,4H),7.25–7.28(m,1H),4.56(s,2H),3.33–3.40(m,1H),1.94–1.96(m,2H),1.76–1.78( m,2H),1.51–1.57(m,1H),1.34–1.40(m,2H),1.26–1.28(m,2H),0.83–0.92(m,1H).

Embodiment 3

[0039] Using tert-butyldimethylsilanol instead of phenethyl alcohol, the others were the same as in Example 1 to obtain the target compound III with a yield of 67%. The reaction formula of benzyl alcohol and tert-butyldimethylsilanol is:

[0040]

[0041] The spectral data of product III is: ESI-MS (m / z): 237[M+H] + ; 1 H-NMR (600MHz, CDCl 3 )δ7.36(d,J=4.5Hz,4H),7.27–7.29(m,1H),4.79(s,2H),0.99(s,9H),0.14(s,6H).

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Abstract

The invention provides a synthetic method of asymmetrical ether in the field of organic synthesis. The general equation of reaction is defined in the specification. In the equation, R-OH is benzyl alcohol, p-methoxy benzyl alcohol, tert-butyl alcohol, diphenyl carbinol or triphenylmethanol; and R'OH is common alkyl alcohol or a compound containing hydroxyl groups. A gold catalyst required by the reaction is Ph3PAuCl, Ph3PAuNTf2, HAuCl4, NaAuCl4, Ph3PAuOTf, Ph3PAuSbF6, IPrAuCl or nano-gold. A medium required by the reaction is solvent-free, and is toluene, mesitylene, 1,2-dichloroethane, tetrahydrofuran, acetonitrile or acetone. The reaction is implemented by heating through a microwave reactor. The method has advantages as follows: raw materials are easily available; operation is simple; the range of application is wide; atom economy is good; and the reaction is green.

Description

technical field [0001] The invention relates to a synthesis method in which two alcohols are directly dehydrated into asymmetric ethers under the action of a gold catalyst under the mediation of microwaves. Background technique [0002] Ethers are a kind of very important structures and play a very important role in organic synthesis. Finding simple and effective methods for the preparation of ethers has always been the focus of organic chemists. (Angew.Chem.Int.Ed., 2007,46,298–300.) Due to the stability of the structure, ethers are often used as protecting groups in organic synthesis. At present, the common classical methods for synthesizing ethers are: [0003] (1) Williamson synthesis method. (Advanced Organic Chemistry, Reactions, Mechanisms and Structure, 4th ed., Wiley, New York, 1992, p1512.), the synthesis method was found in 1850, and the corresponding ether was obtained by reacting halogenated hydrocarbons with sodium alkoxide and sodium phenolate, It is a commo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/09C07C43/164C07C43/188C07C43/205C07C43/17C07C43/12C07C43/115C07F7/08
Inventor 刘永祥程卯生王晓宇石慧杜川王岩石刘洋
Owner SHENYANG PHARMA UNIVERSITY
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