Check patentability & draft patents in minutes with Patsnap Eureka AI!

A kind of heterogeneous synthesis method of dihydrobenzofuran compound

A synthesis method and technology of dihydrobenzene, applied in organic chemistry, chemical recovery, etc., can solve the problems of high toxicity of by-products, harsh reaction conditions, expensive reagents, etc., and achieve the effect of simple operation, readily available raw materials, and mild conditions

Inactive Publication Date: 2019-06-21
NORTHWEST UNIV(CN)
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The above methods have disadvantages such as expensive reagents, high toxicity of by-products or harsh reaction conditions to varying degrees.
Of which visible light / mpg-C 3 N 4 The / air system has the advantages of green and mild reaction conditions, but at present this system only realizes the oxidative coupling of resveratrol and its analogues

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
  • A kind of heterogeneous synthesis method of dihydrobenzofuran compound
  • A kind of heterogeneous synthesis method of dihydrobenzofuran compound
  • A kind of heterogeneous synthesis method of dihydrobenzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]

[0020] Add p-methoxyphenol (0.15 mmol), HFIP 2 mL, styrene (0.3 mmol), 30% H 2 o 2 (20 μL), BiVO 4 (0.12 mmol) and the reaction was stirred at room temperature. Thin-layer chromatography monitors reaction, and after reaction finishes, centrifugation separates catalyzer, washes catalyzer three times with dichloromethane, washes liquid and centrifugation gained supernatant liquid and removes solvent with rotary evaporator, remaining part is with ethyl acetate and sherwood oil as The eluent was separated by column chromatography to obtain the corresponding dihydrobenzofuran as light yellow oily liquid with a yield of 75%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.46 – 7.30 (m, 5H), 6.83 – 6.76 (m, 2H), 6.72 (dd, J = 8.7, 2.6 Hz, 1H), 5.75 (t, J = 8.8 Hz, 1H), 3.78 (s, 3H), 3.61 (dd, J = 15.7, 9.3 Hz, 1H), 3.21 (dd, J = 15.7, 8.2 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 154.3, 153.78, 142.0, 128.7, 128.0, 127.5, 125.8, 113.0, 111.2, 109.2, 84.2, 56.1, 38.9. + ): ...

Embodiment 2

[0023]

[0024] Add p-methoxyphenol (0.15 mmol), HFIP 2 mL, p-chlorostyrene (0.3 mmol), 30% H 2 o 2 (20 μL), BiVO 4 (0.12 mmol) and the reaction was stirred at room temperature. Thin-layer chromatography monitors reaction, and after reaction finishes, centrifugation separates catalyzer, washes catalyzer three times with dichloromethane, removes solvent with rotary evaporator after washing liquid and centrifugation gained supernatant, remaining part uses ethyl acetate and sherwood oil as The eluent was separated by column chromatography to obtain the corresponding dihydrobenzofuran as a light yellow oily liquid with a yield of 87%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.34 (s, 4H), 6.85– 6.77 (m, 2H), 6.71 (dd, J = 8.6, 2.6 Hz, 1H), 5.71 (dd, J = 9.3, 8.1 Hz,1H), 3.77 (s, 3H), 3.60 (dd, J = 15.6, 9.4 Hz, 1H), 3.14 (dd, J = 15.6, 8.0Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 154.4, 153.5, 140.6, 133.7, 128.8, 127.1, 113.0, 111.2, 109.3, 83.4, 56.0, 38.9. HRMS (ESI + ): ...

Embodiment 3

[0027]

[0028] Add p-methoxyphenol (0.15 mmol), HFIP 2 mL, p-fluorostyrene (0.3 mmol), 30% H 2 o 2 (20 μL), BiVO 4 (0.12 mmol) and the reaction was stirred at room temperature. Thin-layer chromatography monitors reaction, and after reaction finishes, centrifugation separates catalyzer, washes catalyzer three times with dichloromethane, removes solvent with rotary evaporator after washing liquid and centrifugation gained supernatant, remaining part uses ethyl acetate and sherwood oil as The eluent was separated by column chromatography to obtain the corresponding dihydrobenzofuran as a light yellow oily liquid with a yield of 81%. 1 H NMR (400 MHz, CDCl 3 ) δ 7.37 (dd,J = 5.3,3.2 Hz, 2H), 7.05 (dt, J = 6.7, 2.0 Hz, 2H), 6.77 (d, J = 8.5 Hz, 2H), 6.71(dd, J = 8.6, 2.6 Hz, 1H), 5.71 (t, J = 8.7 Hz, 1H), 3.77 (s, 3H), 3.59 (dd, J = 15.7, 9.3 Hz, 1H), 3.16 (dd, J = 15.7, 8.2 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ HRMS (ESI + ): m / z [M+Na] + calcd for ...

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 invention discloses a heterogeneous synthesis method of dihydrobenzofuran compounds. This method uses phenol derivatives and styrene derivatives as raw materials, 30% H2O2 as the oxidant, BiVO4 as the heterogeneous catalyst, and hexafluoroisopropanol as the solvent, and stirs at room temperature to synthesize dihydrobenzofuran compounds. The method has the advantages of readily available raw materials, environmentally friendly oxidants, mild conditions, simple operation, and recyclable catalysts.

Description

technical field [0001] The invention relates to a green heterogeneous synthesis method of dihydrobenzofuran compounds, belonging to the technical field of organic synthesis. Background technique [0002] Many pharmaceutically active natural products contain dihydrobenzofuran core skeletons, so the construction of dihydrobenzofuran core skeletons has attracted widespread attention from organic synthetic chemists. According to the different oxidation conditions, the methods reported in the literature to construct dihydrobenzofuran skeletons through the oxidative coupling reaction of phenols and alkenes can be roughly divided into the following two categories: (1) hypervalent iodine reagents, DDQ (2,3- Dichloro-5,6-dicyano-1,4-benzoquinone), one-electron metal oxidant, electrochemical oxidation or Na 2 S 2 o 8 etc. participated in the direct oxidation preparation method. (2) FeCl 3 ·(H 2 O) 6 / DTBP (di-tert-butyl peroxide), FeCl 3 / DDQ, HOTf (trifluoromethanesulfonic ac...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/79C07D307/80
CPCY02P20/584
Inventor 王云侠赵宇崔娜
Owner NORTHWEST UNIV(CN)
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com