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 alcohol

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

Example Embodiment

[0065] Example 1:

[0066]

[0067] After dissolving methyl p-nitrobenzoate (110g, 0.61mol) in methanol (440mL, 4V) and stirring, use pump A to pump into the coil at a speed of 3.16g / min. Sodium borohydride (33.86g, 0.92) mol), MeONa (0.98g, 0.018mol) dissolved in methanol (110mL, 1V) with pump B at a speed of 0.84g / min to pump it In the coil, the coil is immersed in an oil bath at 40°C for a retention time of 60 min. The outlet is sampled by HPLC. The outflowing system is quenched and extracted in a 1L four-necked flask, and then distilled under reduced pressure to obtain 79.3 g of yellow liquid fraction, with a yield of 85. %.

Example Embodiment

[0068] Example 2:

[0069]

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

Example Embodiment

[0071] Example 3:

[0072]

[0073] After dissolving methyl p-nitrobenzoate (110g, 0.61mol) in methanol (440mL, 4V) and stirring, use pump A to pump it into the coil at a speed of 9.48g / min. Sodium borohydride (33.86g, 0.92) mol), MeONa (0.98g, 0.018mol) dissolved in methanol (110mL, 1V) with pump B at a speed of 2.52g / min to pump it to 240mL In the coil, the coil is immersed in an oil bath at 60°C for a retention time of 20 minutes, and the outlet is sampled by HPLC. The outflow system enters a 1L four-neck flask for quenching extraction and then vacuum distillation to obtain a yellow liquid fraction of 88.6g, with a yield of 95 %.

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PUM

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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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