Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing poly-substituted furan through Feist-Benary reaction under alkali-free and solvent-free condition

A multi-substituted furan, solvent-free technology, applied in the field of efficient synthesis of multi-substituted furan compounds, can solve the problems of complicated operation, low yield and the like, and achieves the effects of good regioselectivity, reduced production cost, and easy availability of raw materials

Inactive Publication Date: 2016-12-21
CHONGQING MEDICAL UNIVERSITY
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction needs a large amount of solvent, and two-step reaction, operation is loaded down with trivial details, and productive rate is lower

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing poly-substituted furan through Feist-Benary reaction under alkali-free and solvent-free condition
  • Method for preparing poly-substituted furan through Feist-Benary reaction under alkali-free and solvent-free condition
  • Method for preparing poly-substituted furan through Feist-Benary reaction under alkali-free and solvent-free condition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: 1-chloroacetone reacts with 1,3-cyclohexanedione

[0024]

[0025] In a 50 mL round bottom flask, 1-chlorocyclohexanone (10 mmol) and 1,3-cyclohexanedione (5 mmol) were added. Slowly heated up to 60°C while stirring, the mixture became a homogeneous liquid, and the reaction was continuously monitored by TLC during the reaction. After the reaction, the mixture obtained was directly separated by silica gel column chromatography to obtain furan IIIa1 as a yellow oil with a yield of 85%.

[0026] 1 H NMR (400MHz, CDCl 3 )δ7.06(s, 1H), 2.82(t, J=6.3Hz, 2H), 2.46(dd, J=7.2, 5.8Hz, 2H), 2.19(d, J=1.3Hz, 3H), 2.18- 2.10(m, 2H); 13 C NMR (101MHz, CDCl 3 )δ195.73, 167.42, 138.93, 120.44, 119.10, 38.31, 23.64, 22.76, 9.09; IR (KBr, cm -1 ) 2952, 1667, 1462, 1411, 1071, 573; MS (ESI) calcd for C 9 h 11 o 2 (M+H) + : 151.1, Found: 151.2.

Embodiment 2

[0027] Example 2: Reaction of ethyl 3-bromopyruvate with 1,3-cyclohexanedione

[0028]

[0029] In a 50 mL round bottom flask, ethyl 3-bromopyruvate (10 mmol) and 1,3-cyclohexanedione (5 mmol) were added. While stirring, the mixture was slowly heated up to 80°C and the mixture became a homogeneous liquid, and the reaction was continuously monitored by TLC during the reaction. After the reaction, the mixture obtained was directly separated by silica gel column chromatography to obtain furan IIIc1 as light yellow oil with a yield of 76%.

[0030] 1 H NMR (400MHz, CDCl 3 )δ7.85(s, 1H), 4.31(q, J=7.1Hz, 2H), 2.88(t, J=6.3Hz, 2H), 2.61-2.44(m, 2H), 2.24-2.07(m, 2H ), 1.34(t, J=7.1Hz, 3H); 13 C NMR (101MHz, CDCl 3)δ191.98, 168.33, 161.91, 147.77, 118.73, 117.48, 60.94, 38.71, 23.60, 22.17, 14.19; IR (KBr, cm -1 ): 3451, 3120, 1736, 1554, 1455, 1300, 1183, 1002, 878, 769, 586; MS (ESI) calcdfor C 11 h 13 o 4 (M+H) + : 209.0, Found: 209.1

Embodiment 3

[0031] Example 3: Reaction of ethyl 3-bromopyruvate with 1,3-pentanedione

[0032]

[0033] In a 50 mL round bottom flask, ethyl 3-bromopyruvate (10 mmol) and 1,3-pentanedione (5 mmol) were added. While stirring, the mixture was slowly heated up to 100°C and the mixture became a homogeneous liquid, and the reaction was continuously monitored by TLC during the reaction. After the reaction, the mixture obtained was directly separated by silica gel column chromatography to obtain furan IIIc2 as a yellow oil with a yield of 81%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention provides a poly-substituted furan preparation method, wherein alpha-halogenated ketone reacts with a beta-dicarbonyl compound under an alkali-free and solvent-free condition to obtain the poly-substituted furan compound. According to the present invention, the preparation method has characteristics of easily available raw materials, low cost, mild reaction conditions, simple and easily-controllable operation, less side reaction, simple post-treatment, high product yield, no requirement of any catalysts and solvents, substantially saved production cost, good environmental protection benefits and good economic benefits, and is suitable for the industrial large-scale production.

Description

technical field [0001] The invention relates to a preparation method of multi-substituted furan compounds, in particular to a method for efficiently synthesizing multi-substituted furan compounds with alpha-halogenated ketones and beta-dicarbonyl compounds as raw materials. Background technique [0002] Furan is an important five-membered heterocyclic compound, which plays an important role in chemical, biological and pharmaceutical research. Many natural products contain a furan ring core structure. These furan derivatives usually have certain biological activities, such as antibacterial, Insecticidal, anti-tumor, sedative and other effects. [0003] There are many reports on the synthesis of furan compounds, such as under the catalysis of Bronsted acid or Lewis acid, 1,4-dicarbonyl compounds are prepared by condensation reaction (Paal-Knorr furan synthesis reaction); with alkenes and alkynes as substrates , prepared by transition metal catalyzed cyclization reaction; simp...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D307/84C07D307/68
CPCC07D307/68C07D307/84
Inventor 唐强罗娟
Owner CHONGQING MEDICAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com