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Method for preparing ether compound

A kind of ether compound, the technology of compound, is applied in the field of preparing ether compound represented by the following formula, can solve the problem such as being difficult to use

Active Publication Date: 2016-03-09
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, bis(chloromethyl)ether is a very reactive compound and it is not readily available in industry

Method used

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  • Method for preparing ether compound
  • Method for preparing ether compound
  • Method for preparing ether compound

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preparation example Construction

[0048] The preparation of the compound represented by the formula (1) is described below.

[0049] The compound represented by the formula (1) can be prepared by reacting bis(acetoxymethyl) ether with the compound represented by the formula (2):

[0050]

[0051] where n and X have the same meaning as above.

[0052] The reaction is usually carried out in an organic solvent in the presence of a metal catalyst.

[0053]Examples of the compound represented by the formula (2) include phenol, 4-chlorophenol, 4-nitrophenol, 4-cyanophenol, 2,4-dichlorophenol, 2,4,6-trichlorophenol, 2, 3,6-Trichlorophenol, 2,3,5,6-Tetrachlorophenol, 2,3,4,6-Tetrachlorophenol, 2,3,4,5,6-Pentachlorophenol, 2,6- Dichloro-4-nitrophenol, 2,6-dichloro-4-cyanophenol, 2,4,6-tribromophenol, 2,3,4,5,6-pentabromophenol, 2,6- Dibromo-4-cyanophenol and 2,3,4,5,6-pentafluorophenol.

[0054] Examples of the organic solvent include toluene, xylene, mesitylene, dichlorobenzene, and o-dichlorobenzene. Preferen...

Embodiment

[0064] Hereinafter, the present invention will be further specifically described with reference to Examples and the like.

[0065] First, the preparation example of the ether compound is described.

preparation example 1-1

[0066] Preparation Example 1-1 (Steps A to C)

[0067] To 800 ml of 2-methoxyethanol, 100 g (purity 95.0 g) of bis(2,4,6-trichlorophenoxymethyl) ether containing 5 wt% alumina and 50% water were added of 91.4 g (pure content 45.7 g, 3.0 equiv.) of sodium methanethiolate, followed by stirring at 100 to 105° C. for 4 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature and filtered. Thereafter, hexane and 10% aqueous NaOH solution were added, followed by stirring. The mixture was left to stand and then separated. The obtained organic solvent layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under normal pressure, whereby 32.2 g of bis(methylthiomethyl)ether (referred to as compound Y) was obtained as a residue. .

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Abstract

An ether compound represented by a formula (3) (wherein R represents alkyl having 1 to 6 carbon atoms) can be prepared by the following method. The method comprises the steps: step A, a compound (wherein n represents 0-5 of integer, X represents halogen atom, containing alkyl having 1-3 carbon atoms, cyano, nitro or trifluoromethyl) expressed by formula (1) reacts with 1-6 carbon atom-containing metal alkane thiolate in 2-methoxyethanol; step B, a reaction mixture obtained from step A is added water and a hydrocarbon solvent having 5-8 carbon atoms, and an organic layer is separated; step C, the solvent is distilled in the organic layer obtained from the step B to prepare bis(alkylthiolmethyl)ether; and step D, the bis(alkylthiolmethyl)ether obtained from step C reacts with 2-cyanoethanol and a halogenating agent in the ether solvent.

Description

technical field [0001] The present invention relates to a method for producing an ether compound represented by the following formula (3). Background technique [0002] The ether compound represented by the formula (3) is used to prepare a phosphoramidite of a nucleotide: [0003] [0004] wherein R represents an alkyl group having 1 to 6 carbon atoms. The ether compound represented by formula (3) can be prepared from bis(chloromethyl)ether (see WO2013 / 027843). However, bis(chloromethyl)ether is a very reactive compound and it is not easy to use in industry. [0005] For the preparation of α,α'-disaturated dimethyl ethers, it has been suggested to use bis(aryloxymethyl)ethers instead of bis(chloromethyl)ethers (see USP-3,954,878, JPHei04-036269A). SUMMARY OF THE INVENTION [0006] The present invention provides a method for preparing an ether compound represented by formula (3), the method comprising: [0007] Step A: The compound represented by the formula (1): ...

Claims

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Application Information

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IPC IPC(8): C07C323/12C07C319/20
CPCC07C319/02C07C323/12
Inventor 田中雄树井原秀树
Owner SUMITOMO CHEM CO LTD
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