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Method for synthesizing a-hydroxycarboxylate from 2-hydroxypropanedicyanide

A technology of hydroxymalonocyanide and hydroxycarboxylate, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, and can solve problems such as high cost, complicated operation and post-processing, and long reaction time. To achieve the effect of short reaction time, clean reaction and high yield

Active Publication Date: 2016-08-17
SHANGHAI SYNTHEALL PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the technical problems of complex operation and post-treatment, long reaction time and high cost in the existing method for synthesizing a-hydroxycarboxylate

Method used

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  • Method for synthesizing a-hydroxycarboxylate from 2-hydroxypropanedicyanide
  • Method for synthesizing a-hydroxycarboxylate from 2-hydroxypropanedicyanide
  • Method for synthesizing a-hydroxycarboxylate from 2-hydroxypropanedicyanide

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Experimental program
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Effect test

Embodiment 1

[0015]

[0016] Benzaldehyde (106 mg, 1 mmol) was dissolved in 2 mL of methanol, acetic acid solution of 2-hydroxypropanedicyanide (1 mL, 1 mol / L) was added, and then 4-dimethylaminopyridine (12 mg) was added rapidly, and stirred at 0°C 10 minutes. The reaction solution was concentrated and separated by column chromatography to obtain methyl α-hydroxyphenylacetate (151 mg, 91%). 1 H NMR (400 MHz, CD 3 OD) δ7.36-7.29 (m, 5H), 5.17 (s, 1H), 3.67 (s, 3H).

Embodiment 2

[0018]

[0019] 3,4-Dimethoxybenzaldehyde (166 mg, 1 mmol) was dissolved in 2 mL of methanol, and 2-hydroxypropanedicyanide in trifluoroacetic acid (0.4 mL, 5mol / L) was added, followed by the rapid addition of 4-dimethoxy Aminopyridine (12mg), stirred at room temperature for 40 minutes. The reaction solution was concentrated and separated by column chromatography to obtain methyl α-hydroxy-3,4-dimethoxyphenylacetate (199 mg, 88%). 1 H NMR (400 MHz, CD 3 OD) δ 7.03 (d, J=1.6 Hz, 1H), 7.95-7.92 (m, 2H), 5.11 (s, 1H), 3.82 (s, 3H), 3.81 (s, 3H), 3.68 (s, 3H ).

Embodiment 3

[0021]

[0022] 2-Formaldehyde furan (96 mg, 1 mmol) was dissolved in 2 mL of methanol, and 2-hydroxypropanedicyanide in trifluoroacetic acid solution (0.2 mL, 10mol / L) was added, and then 4-dimethylaminopyridine (12 mg) was added rapidly , stirred at room temperature for 100 minutes. The reaction solution was concentrated and separated by column chromatography to obtain methyl α-hydroxy-2-furanacetate (137 mg, 86%). 1 H NMR (400MHz, CD 3 OD) δ 7.46-7.45 (m, 1H), 6.38-6.37 (m, 2H), 5.21 (s, 1H), 3.73 (s,3H).

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Abstract

The invention relates to synthesis of alpha-hydroxy carboxylic ester with 2-hydroxy propylene cyanide and corresponding aldehyde or ketone. The existing common alpha-hydroxy carboxylic ester generally needs superior cyan such as trimethylsilyl cyanide, and then hydrolysis is carried out on the cyan, so that the reaction operation is relatively complicated, and post treatment is a trouble. According to the method, 2-hydroxy propylene cyanide and corresponding aldehyde or ketone are mixed directly, 4-dimethylamino-pyridne of the catalysis amount is added, alcohol compound is taken as the solvent, and the product can be obtained by stirring for 10-120 minutes. The method for synthesizing the alpha-hydroxy carboxylic ester is safe and has high efficiency.

Description

technical field [0001] The invention relates to a method for synthesizing alpha-hydroxy carboxylate from 2-hydroxymalonocyanide. Background technique [0002] The chemical synthesis method of present common α-hydroxycarboxylate is as follows: [0003] 1) Use trimethylsilyl cyanide and zinc iodide to add cyano groups, and then hydrolyze the cyano groups. The reaction operation is relatively complicated. Bioorganic & Medicinal Chemistry (Bioorganic & Medicinal Chemistry, 19(22), 6935-6948; 2011 ) discloses its synthesis method, and the reaction formula is as follows: [0004] [0005] 2) Use trimethylsilyl chloride and phosphorus hexafluoride tetrabutylamine to react with the substrate, then add tetrabutylamine carbonate to generate trimethylsilyl-protected a-hydroxy carboxylate, and then use tetrabutylammonium fluoride Deprotection yields the product. The operation and post-treatment are complicated, the purification is difficult, and the cost is high. . [0006] . ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/22C07C69/732C07C69/734C07C205/56C07C201/12C07D307/54C07D213/55C07D277/30C07D207/327C07D239/30
Inventor 张治柳林小娟于海宇吴成德马汝建陈曙辉
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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