A kind of method that carbonyl is reduced to alcohol under room temperature air atmosphere

An air and atmosphere technology, applied in chemical instruments and methods, reduction preparation of oxygen-containing functional groups, preparation of organic compounds, etc., can solve the problems of unfavorable catalyst application, complex catalyst structure, poor substrate applicability, etc., and achieve low cost and toxicity Small, low toxicity effects

Inactive Publication Date: 2020-06-12
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Alcohols, formic acid and its salts, lithium aluminum hydride, hydrazine hydrate, etc. are common hydrogen donors in catalytic transfer hydrogenation. These hydrogen donors are often used for the reduction of carbonyl compounds, but these hydrogen donors have high toxicity and poor reduction effect. shortcoming
In addition, there are many shortcomings in the catalytic transfer hydrogenation reduction reaction currently reported, such as the need to use some transition metal catalysts or the use of complex ligands, many of which have complex structures and cumbersome preparation methods, which are not conducive to the practical use of catalysts. application
In addition, among the many reports on carbonyl reduction, many reports have poor applicability to substrates, and some methods are even only applicable to several specific aldehyde and ketone substrates.

Method used

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  • A kind of method that carbonyl is reduced to alcohol under room temperature air atmosphere
  • A kind of method that carbonyl is reduced to alcohol under room temperature air atmosphere
  • A kind of method that carbonyl is reduced to alcohol under room temperature air atmosphere

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of benzyl alcohol

[0044] Take a 25mL reaction bottle and put a magnet into the bottle. Weigh benzaldehyde (0.080g, 0.75mmol), potassium 4-carboxyphenyltrifluoroborate (2.5% eq.4.4mg), add 3mL methanol as solvent to the reaction bottle, and then pipette the triethoxy base silane (2.2eq.306μL), react in air atmosphere at room temperature. The reaction process was detected by TLC. After 8 hours, it was extracted with dichloromethane (3×40mL), the dichloromethane phases were combined, washed with 40mL deionized water, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. Color liquid product 64mg, yield 72%; NMR is as follows:

[0045] 1 H NMR (500MHz, CDCl 3 ): δ7.40–7.28(m,5H),4.66(d,J=5.6Hz,2H),2.25(s,1H). 13 C NMR (125MHz, CDCl 3 ): δ140.80, 128.46, 127.53, 126.92, 65.15.

Embodiment 2

[0046] Embodiment 2: the synthesis of p-bromobenzyl alcohol

[0047] Take a 25mL reaction bottle and put a magnet into the bottle. Weigh p-bromobenzaldehyde (0.139g, 0.75mmol), potassium phenyl trifluoroborate (2.5% eq. 3.5mg), add 3mL methanol as solvent to the reaction bottle, and then pipette the triethoxy Silane (2.2eq.306μL), react in air at room temperature. The reaction process was detected by TLC. After 20 minutes, it was extracted with dichloromethane (3×40mL), the dichloromethane phases were combined, washed with 40mL deionized water, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. Column chromatography gave white Solid product 131mg, yield 93%; NMR is as follows:

[0048] 1 H NMR (500MHz, CDCl3 ): δ7.47(d, J=8.3Hz, 2H), 7.22(d, J=8.1Hz, 2H), 4.62(d, J=5.8Hz, 2H), 2.05(t, J=5.9Hz, 1H ). 13 C NMR (125MHz, CDCl 3 ): δ139.70, 131.56, 128.53, 121.38, 64.46.

Embodiment 3

[0049] Embodiment 3: the synthesis of 2,6-dichlorobenzyl alcohol

[0050] Take a 25mL reaction bottle and put a magnet into the bottle. Weigh 2,6-dichlorobenzaldehyde (0.131g, 0.75mmol), potassium phenyltrifluoroborate (2.5%eq.3.5mg), add 3mL methanol as solvent to the reaction bottle, and then pipette Trimethoxysilane (2.2eq.202μL) was reacted in air at room temperature. The reaction process was detected by TLC. After 10 minutes, it was extracted with dichloromethane (3×40mL), the dichloromethane phases were combined, washed with 40mL deionized water, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation. Column chromatography gave white Solid product 120mg, yield 90%; NMR is as follows:

[0051] 1 H NMR (500MHz, CDCl 3 ): δ7.31(d, J=8.1Hz, 2H), 7.20–7.13(m, 1H), 4.94(d, J=5.9Hz, 2H), 2.33(t, J=6.3Hz, 1H). 13 CNMR (125MHz, CDCl 3 ): δ135.89, 135.58, 129.72, 128.38, 60.05.

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Abstract

The invention belongs to the field of organic synthesis and relates to a method of reducing carbonyl compound into alcohol in air atmosphere at room temperature. The method includes: firstly, adding methanol, a catalyst and the carbonyl compound into a reaction bottle and slowly adding silane into the reaction bottle, magnetically stirring the components and carrying out a reaction for 10 min to 8hours in air atmosphere at room temperature to obtain a mixture containing a benzyl compound after the reaction is finished; secondly, extracting the mixture containing the benzyl compound with an extraction agent dichloromethane, mixing organic phases, and washing the organic phases with a washing agent deionized water, drying the organic phases with anhydrous sodium sulfate, and evaporating theorganic phases to remove a solvent and obtain a crude product of a benzyl alcohol compound; finally, separating and purifying the crude product through column chromatography to prepare a pure productof the benzyl alcohol compound. In the method, a reducing agent is low in toxicity and is clean and environment-friendly. The method is free of a noble metal catalyst and is low in cost, is gentle inreaction conditions, and can reach high selectivity and yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for reducing a carbonyl group to benzyl alcohol under an air atmosphere at room temperature, in particular to using potassium phenyltrifluoroborate as a catalyst and triethoxysilane as a reducing agent to reduce a carbonyl group to an alcohol Methods. [0002] technical background [0003] Alcohol compounds are common substances in people's lives, and are also important chemical raw materials, widely used in the synthesis of chemicals such as pesticides, medicines, and spices. The reduction of carbonyl compounds to alcohols is one of the common ways to prepare alcohols, the most typical of which is the reduction of aldehydes and ketones to alcohols. [0004] There are many reports on the reduction of aldehydes and ketones to alcohols. Among them, catalytic transfer hydrogenation is a relatively common method for reducing carbonyl groups. This method is widely used by scie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/14C07C33/22C07C33/46C07C33/28C07C33/32C07C201/12C07C205/19C07C253/30C07C255/53C07D213/30
CPCC07C29/14C07C201/12C07C253/30C07D213/30C07C33/22C07C33/46C07C33/28C07C33/32C07C205/19C07C255/53
Inventor 刘建辉王星旸郁亚强
Owner DALIAN UNIV OF TECH
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