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Method for preparing alpha-keto ester by microfluidic chip reactor

A microfluidic chip and reactor technology, applied in chemical instruments and methods, formation/introduction of carboxylate groups, preparation of carboxylate esters, etc., can solve the problems of long reaction process cycle, harsh reaction conditions, and poor economy, etc. Achieve the effect of good industrial scale-up potential, mild reaction conditions and high safety

Active Publication Date: 2017-10-20
NANJING UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The technical problem to be solved by the present invention is to provide a method for continuously preparing α-keto esters using a microfluidic chip reactor to solve the problems of poor economy, harsh reaction conditions, long reaction process cycle and high energy consumption in the prior art.

Method used

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  • Method for preparing alpha-keto ester by microfluidic chip reactor
  • Method for preparing alpha-keto ester by microfluidic chip reactor
  • Method for preparing alpha-keto ester by microfluidic chip reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis of compound 3a:

[0035] Dissolve 2mmol (0.24g) of acetophenone, 10mmol (1.22g) of phenylethyl alcohol, 0.6mmol (0.15g) of iodine, and 2mmol (0.30g) of 1,8-diazabicyclo[5.4.0]undecene (DBU). In 3mL N,N-dimethylformamide (DMF), a homogeneous solution A was obtained, which was added to the microsyringe pump a; 8mmol (1.02g) of 70% tert-butanol hydroperoxide solution was dissolved in 3 mLN, In N-dimethylformamide (DMF), a homogeneous solution B was obtained, which was added to microsyringe pump b; saturated sodium thiosulfate was added to microsyringe pump c; microsyringe pumps a, b, c The injection flow rate was 5 μl / min, the microfluidic chip reaction volume V=10 μl (reaction time 1min), and the reactor temperature was 130°C; after two cycles of reaction (2min), the reaction liquid was collected, and the product yield was calculated by HPLC. The yield was 84%, and the product 3a was obtained after separation by column chromatography; 1 H NMR (400MHz, CDCl 3 ...

Embodiment 2

[0037]Synthesis of compound 3b:

[0038] 2mmol (0.31g) p-chloroacetophenone, 10mmol (1.22g) phenylethyl alcohol, 0.6mmol (0.15g) iodine, 2mmol (0.30g) 1,8-diazabicyclo [5.4.0] undecene (DBU ) was dissolved in 3mL N,N-dimethylformamide (DMF) to obtain a homogeneous solution A, which was added to the microsyringe pump a; 8mmol (1.02g) 70% tert-butanol hydroperoxide solution was dissolved in 3mLN , in N-dimethylformamide (DMF), to obtain a homogeneous solution B, which was added to microinjection pump b; saturated sodium thiosulfate was added to microinjection pump c; microinjection pumps a, b, c The injection flow rate is 5 μl / min, the microfluidic chip reaction volume V=10μl (reaction time 1min), and the reactor temperature is 130°C; after two cycles of reaction (2min), the reaction liquid is collected and calculated by HPLC The product yield was 88%, and the product 3b was obtained after separation by column chromatography; 1 H NMR (400MHz, CDCl3) δ7.80 (dd, J = 8.9, 5.4Hz, ...

Embodiment 3

[0040] Synthesis of compound 3c:

[0041] 2mmol (0.33g) m-nitroacetophenone, 10mmol (1.22g) phenethyl alcohol, 0.6mmol (0.15g) iodine, 2mmol (0.30g) 1,8-diazabicyclo [5.4.0] undecene ( DBU) was dissolved in 3 mL N,N-dimethylformamide (DMF) to obtain a homogeneous solution A, which was added to the microsyringe pump a; 8 mmol (1.02 g) of 70% tert-butanol hydroperoxide solution was dissolved in In 3mL N,N-dimethylformamide (DMF), obtain a homogeneous solution B, which is added to microsyringe pump b; saturated sodium thiosulfate is added to microsyringe pump c; microsyringe pumps a, b, The injection flow rate of c is 5 μl / min, the microfluidic chip reaction volume V=10μl (reaction time 1min), and the reactor temperature is 130°C; after two cycles of reaction (2min), the reaction liquid is collected and analyzed by HPLC The calculated product yield was 86%, and the product 3c was obtained after column chromatography separation; 1 H NMR (400MHz, CDCl 3 )δ8.86–8.64(m,1H),8.33(dd...

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Abstract

The invention discloses a method for preparing alpha-keto ester by a microfluidic chip reactor. The method comprises the steps as follows: acetophenone compounds, alcohol, iodine and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) are dissolved in DMF for obtaining a homogeneous solution A; tert-butanol aqueous hydrogen peroxide in a corresponding ratio is dissolved in DMF for obtaining a homogeneous solution B; a saturated sodium thiosulfate solution is prepared for quenching a reaction solution; after the homogeneous solution A, the homogeneous solution B and a quenching solution are injected into a microfluidic chip and reactants are mixed, reacted and quenched in the chip, alpha-keto ester is obtained after aftertreatment. Compared with the prior art, the method is simple, convenient and safe to operate, efficient and capable of realizing continuous preparation of alpha-keto ester, adopts mild reaction conditions and has good substrate universality.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for continuously preparing α-keto esters using a microfluidic chip reactor. Background technique [0002] α-Ketoesters and their derivatives are simple and special compounds with two adjacent carbonyl groups. Due to the large number of reaction centers, they have more special chemical properties than ordinary compounds. They are used in organic synthesis and biological It plays a connecting role in the metabolic process. It is an intermediate in the synthesis of various heterocyclic compounds, sugars, proteins, ribose, enzyme inhibitors, enzyme substrates, and alkaloids. It can be used as the digestive precursor and synthesis of many substances. Precursors are also widely used in the synthesis and development of drugs, including antineoplastic drugs, antihypertensive drugs, antiviral drugs, and so on. At present, certain structures of α-ketoesters have been ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/00C07C69/738C07C201/12C07C205/56C07D333/24C07D333/16C07B41/12
CPCC07B41/12C07C67/00C07C201/12C07D333/16C07D333/24C07C69/738C07C205/56
Inventor 郭凯郭诗宇方正李昕朱宁万力张锴欧阳平凯
Owner NANJING UNIV OF TECH
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