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Borohydride reduction stabilizing system and method for reducing ester into alcohol

A borohydride and stable system technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve problems such as easy decomposition, reduce hydrogen generation, reduce excessive use, and reduce process risks Effect

Inactive Publication Date: 2019-08-23
ASYMCHEM LAB TIANJIN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The main purpose of the present invention is to provide a kind of borohydride reducing stable system and the method that esters are reduced to alcohols, to solve the easy decomposition problem when sodium borohydride / potassium is used as reducing agent to reduce esters to alcohols in the prior art question

Method used

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  • Borohydride reduction stabilizing system and method for reducing ester into alcohol
  • Borohydride reduction stabilizing system and method for reducing ester into alcohol
  • Borohydride reduction stabilizing system and method for reducing ester into alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066]

[0067] After dissolving methyl p-nitrobenzoate (110g, 0.61mol) in methanol (440mL, 4V) and stirring, pump A into the coil at a speed of 3.16g / min, sodium borohydride (33.86g, 0.92 mol), MeONa (0.98g, 0.018mol) was dissolved in methanol (110mL, 1V) and pumped to In the coil tube, the coil tube was immersed in an oil bath at 40°C, the retention time was 60min, the outlet was sampled by HPLC, and the outflow system was put into a 1L four-neck flask for quenching and extraction, and then vacuum distillation gave 79.3g of yellow liquid fraction product, with a yield of 85% %.

Embodiment 2

[0069]

[0070] Methyl p-nitrobenzoate (110g, 0.61mol) was dissolved in methanol (440mL, 4V) and stirred, then pumped into the coil with pump A at a speed of 4.74g / min, sodium borohydride (33.86g, 0.92 mol), MeONa (0.98g, 0.018mol) were dissolved in methanol (110mL, 1V) and pumped to 240mL with pump B at a speed of 1.26g / min In the coil, the coil is immersed in an oil bath at 50°C, the retention time is 40min, the outlet is sampled by HPLC, and the outflow system enters a 1L four-neck flask for quenching and extraction, and then vacuum distillation to obtain 84g of yellow liquid fraction product, with a yield of 90.3% .

Embodiment 3

[0072]

[0073] Methyl p-nitrobenzoate (110g, 0.61mol) was dissolved in methanol (440mL, 4V) and stirred, then pumped into the coil with pump A at a speed of 9.48g / min, sodium borohydride (33.86g, 0.92 mol), MeONa (0.98g, 0.018mol) were dissolved in methanol (110mL, 1V) and pumped to 240mL with pump B at a speed of 2.52g / min In the coil tube, the coil tube was submerged in a 60°C oil bath, the retention time was 20min, the outlet was sampled by HPLC, and the outflow system was put into a 1L four-necked flask for quenching and extraction, and then vacuum distillation to obtain 88.6g of yellow liquid fraction product, with a yield of 95% %.

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Abstract

The invention provides a borohydride reduction stabilizing system and a method for reducing ester into alcohol. The borohydride reduction stabilizing system comprises a borohydride reducing agent anda stabilizer for stabilizing the borohydride reducing agent, wherein the borohydride reducing agent is sodium borohydride or potassium borohydride, and the stabilizer is an alkali metal salt of alcohol. On the basis of an existing sodium borohydride / potassium reducing agent, an alcohol alkali metal salt (such as sodium alcoholate or potassium alcoholate) is added, and then the sodium borohydride / potassium reducing agent can keep stable and is not decomposed under a heating condition, so that on one hand, reduction activity is maintained in a relatively high state and the situation of excessiveuse is reduced, and on the other hand, generation of hydrogen is reduced and the process risk is reduced.

Description

technical field [0001] The invention relates to the field of ester reduction, in particular to a borohydride reduction stabilization system and a method for reducing esters to alcohols. Background technique [0002] In the field of pharmaceutical and chemical industry, it is often encountered that the process synthesis technology of realizing the reduction of ester group to alcohol compound through continuous reaction technology. The reduction of ester groups to the corresponding alcohols is an important synthetic method for the conversion of an important functional group in organic synthesis. The commonly used reducing reagents are metal hydrides, such as lithium aluminum hydride, lithium borohydride, diisobutyl aluminum hydride, etc. And this kind of reagent is usually sensitive to water, and sodium borohydride is relatively water-sensitive, and has the prospect of industrial application. [0003] However, sodium borohydride will not have strong reducibility to some ester...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C29/147C07C31/20C07C31/125C07C201/12C07C205/19C07C213/00C07C215/08C07C215/20C07C215/28C07D213/30C07D239/42C07D471/14C07D473/00
CPCC07B41/02C07C29/147C07C201/12C07C213/00C07D213/30C07D239/42C07D471/14C07D473/00C07C2601/14C07C205/19C07C215/08C07C215/20C07C215/28C07C31/20C07C31/125
Inventor 洪浩卢江平张恩选刘志清张涛
Owner ASYMCHEM LAB TIANJIN
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