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Method for preparing hydroxyl phosphonate

A technology of hydroxyphosphonate and hydrogen phosphine, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., to achieve high yield, mild reaction conditions, and short reaction time

Inactive Publication Date: 2014-09-17
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] So far, there is no report on the preparation of hydroxyphosphonates by alkali metal compounds as single-component catalysts for the hydrophosphination of aldehydes and ketones

Method used

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  • Method for preparing hydroxyl phosphonate
  • Method for preparing hydroxyl phosphonate
  • Method for preparing hydroxyl phosphonate

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Example 1: 2,6-Diisopropylanilinide lithium catalyzes the reaction of benzaldehyde and diethyl phosphite

[0034] Under anhydrous, oxygen-free and argon protection, diethyl phosphite (0.77mL, 6mmol) and 2,6-diisopropylanilinidelithium (0.005mmol) were successively added to a 30mL Schlenk reaction flask, and at room temperature After stirring for 10 minutes, benzaldehyde (0.51 mL, 5 mmol) was added, and after reacting at room temperature for 5 minutes, deionized water was added to terminate the reaction. Extracted with ethyl acetate (10mL×3), dried overnight with anhydrous sodium sulfate, filtered, spin-dried, washed with n-hexane to obtain a white solid, dried to constant weight to obtain 1.21 grams of α-hydroxyphosphonate, the calculated yield was 99%.

[0035] The nuclear magnetic analysis for this α-hydroxy phosphonate is as follows: 1 H NMR (CDCl 3 ,400MHz,ppm)δ7.50-7.48(2H,m,ArH),7.37-7.28(3H,m,ArH),5.03-5.00(1H,d,J=10.8Hz,CH),4.08-3.94(4H ,m,CH 2 ), 3.62 (1H,...

Embodiment 2

[0036] Example 2: 2,6-diisopropylanilinide lithium catalyzes the reaction of benzaldehyde and diethyl phosphite

[0037] Under anhydrous, oxygen-free and argon protection, diethyl phosphite (0.77 mL, 6 mmol), 2,6-diisopropylanilinide lithium (0.005 mmol), n-hexane ( 2 mL), stirred at room temperature for 10 minutes, then added benzaldehyde (0.51 mL, 5 mmol), and reacted at room temperature for 5 minutes, then added deionized water to terminate the reaction. Extracted with ethyl acetate (10mL×3), dried overnight with anhydrous sodium sulfate, filtered, spin-dried, washed with n-hexane to obtain a white solid, dried to constant weight to obtain 1.21 grams of α-hydroxyphosphonate, the calculated yield was 99%.

Embodiment 3

[0038] Example Three: 2,6-Diisopropylanilinide Lithium Catalyzed Reaction of Benzaldehyde and Diethyl Phosphite

[0039] Under anhydrous, oxygen-free and argon protection, diethyl phosphite (0.77mL, 6mmol) and 2,6-diisopropylanilinidelithium (0.05mmol) were successively added to a 30mL Schlenk reaction flask, and After stirring for 10 minutes, benzaldehyde (0.51 mL, 5 mmol) was added, and after reacting at room temperature for 5 minutes, deionized water was added to terminate the reaction. Extracted with ethyl acetate (10mL×3), dried overnight with anhydrous sodium sulfate, filtered, spin-dried, washed with n-hexane to obtain a white solid, dried to constant weight to obtain 1.21 grams of α-hydroxyphosphonate, the calculated yield was 99%.

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Abstract

The invention discloses a method for preparing hydroxyl phosphonate. According to the method, an alkali metal compound is used as a monocomponent catalyst to catalyze a hydrogen phosphonylation reaction of aldehyde or ketone so as to prepare hydroxyl phosphonate. The alkali metal compound is one compound selected from n-butyllithium, 2,6-lithium diisopropyl aniline, 2,6-sodium diisopropyl aniline, 2,6-potassium diisopropyl aniline, 2,6-lithium dimethylaniline, 2,6-sodium dimethylaniline, 2,6-potassium dimethylaniline, phenylamino lithium, phenylamino sodium, phenylamino potassium, bi(trimethylsilyl) amido lithium, bi(trimethylsilyl)amido sodium, bi(trimethylsilyl)amido potassium, lithium diisopropylamide, sodium diisopropylamide and potassium diisopropylamide. The method provided by the invention has advantages as follows: catalytic activity is high; reaction time is short; dosage of the catalyst can be reduced to one thousand; reaction conditions are mild; yield is high; and the method has good universality for aldehyde and ketone substrates.

Description

technical field [0001] The invention relates to the field of catalysts, in particular to a method for preparing hydroxyphosphonate by using an alkali metal compound as a single-component catalyst to catalyze the hydrophosphination reaction of aldehydes or ketones. Background technique [0002] In the past two decades, the application of phosphorus-containing organic compounds, especially the derivatives of α-hydroxyphosphonic acid and α-hydroxyphosphonic acid, in medicinal chemistry has attracted a lot of attention. Studies have shown that α-hydroxyphosphonic acid compounds It has a variety of biological activities, such as pesticides, antibiotics, anticancer agents, antiviral agents, and enzyme inhibitors, etc. Therefore, it is important to study the efficient synthesis of α-hydroxyphosphonate. significance. [0003] There are many ways to synthesize α-hydroxyphosphonate, and hydrogen phosphine reaction is undoubtedly the most environmentally friendly and atom-economical s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40
Inventor 姚英明刘承伟
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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