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A kind of method of synthesizing furan compound

A compound and furan technology, applied in the field of organic compound synthesis, can solve the problems of 2-chloro-n-valeraldehyde, which is a raw material that is not readily available, dangerous use of diisopropylamide lithium, and complicated reaction processes, and achieves substrate adaptability. Good, easy to obtain raw materials, simple reaction steps

Active Publication Date: 2021-03-19
ZHEJIANG UNIV OF TECH
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Problems solved by technology

[0007] In 2013, Chang, Stanley found a kind of acetophenone as raw material, under the effect of lithium diisopropylamide, condensed with 2-chloro-n-valeraldehyde, and then refluxed for 12 hours to obtain the method of target product ( European Journal of Organic Chemistry, 2013 (16), 3219-3222; 2013) but this method exists reaction process too complicated, and this raw material of 2-chloro-n-pentanal is not easy to get, and lithium diisopropylamide is more dangerous when using, and reaction Harsh conditions and only moderate yields

Method used

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  • A kind of method of synthesizing furan compound
  • A kind of method of synthesizing furan compound
  • A kind of method of synthesizing furan compound

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preparation example Construction

[0035] The preparation process of gold catalyst described in the embodiment is:

[0036] Synthesis of A: Add 5-bromoisoquinoline (10mmol), 2-bromophenylboronic acid (1.06equiv.), tetrakis(triphenylphosphine) palladium (5mol%), carbonic acid Sodium hydrogen (4.5 equiv.), and under nitrogen protection, add 20ml of ethylene glycol dimethyl ether and 10ml of deionized water into the bottle with a syringe, and heat the system to 95°C to react overnight. After the reaction, cool to room temperature, extract with dichloromethane, collect the organic phase, and extract the water phase twice, combine the organic phase, wash the organic phase with water, and dry with anhydrous sodium sulfate, then use column chromatography Product A was isolated.

[0037] Synthesis of B: Add A (10 mmol) and 30 ml tetrahydrofuran into a round-bottomed flask equipped with a magnet, add methyl iodide (1.5 equiv.) under stirring at room temperature, and react for 24 hours. After the reaction, a large numb...

Embodiment 1

[0044]

[0045] 0.004mmol Add 0.02mmol tetrakis(3,5-bis(trifluoromethyl)phenyl)sodium borate into a 15ml Schlenck tube, after the nitrogen protection is completed, add 0.2mmol 1-phenylhept-2-yn-1-one with a syringe and 2mL DCE. Then, react at 60 degrees Celsius for 2 hours. After the reaction, add two tablespoons of column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure, and then separate the pure product by column chromatography (using petroleum ether as eluent). The material was a yellow liquid in 96% yield.

[0046] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ7.69(dd,J=8.4,1.1Hz,2H), 7.41–7.38(m,2H),7..27–7.24(m,1H),6.60(d,J=3.2Hz,1H), 6.11(d, J=3.2Hz, 1H), 2.71(t, J=7.4Hz, 2H), 1.81-1.73(m, 2H), 1.05(t, J=7.4Hz, 3H). 13 C NMR (125MHz, CDCl 3 )δ156.28, 152.18, 131.33, 128.58, 126.71, 123.35, 106.98, 105.64, 30.22, 21.47, 13.76.

Embodiment 2

[0048]

[0049] 0.01mmol Add 0.02mmol tetrakis(3,5-bis(trifluoromethyl)phenyl)sodium borate into a 15ml Schlenck tube, after the nitrogen protection is completed, add 0.2mmol 1-(3-bromophenyl)hept-2- Alkyn-1-one and 2 mL DCE. Next, react at 60 degrees Celsius for 2 hours. After the reaction, add two tablespoons of column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure, and then separate the pure product by column chromatography (using petroleum ether as eluent). The material was a yellow liquid and the yield was 93%.

[0050] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ7.82(dd,J=7.9,1.7Hz,1H), 7.65(dd,J=8.0,1.1Hz,1H),7.39–7.32(m,1H),7.13(d,J=3.3Hz, 1H ),7.12–7.07(m,1H),6.16(d,J=3.3Hz,1H),2.70(t,J=7.5Hz, 2H),1.84–1.70(m,2H),1.04(t,J= 7.4Hz, 3H). 13 C NMR (125MHz, CDCl 3 )δ156.48, 149.45, 134.09, 131.55, 128.32, 127.74, 127.28, 119.16, 111.48, 106.93, 30.15, 21.42, 13.78.

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Abstract

The invention discloses a method for synthesizing furan compounds. The method includes heating and reacting an acetyenic ketone shown as a formula I as an initial raw material to 25-80 DEG C for 2-6 hin the presence of a gold catalyst, sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate and a solvent; and subjecting an obtained reaction solution to separation and purification to obtain a furancompound shown as a formula II. The method is safe, environment-friendly, and free of waste gas and wastewater, raw materials are easily available, substrate adaptability is good, cyclization can be efficiently achieved for various substituent groups, reaction time is short, reaction condition is mild, reaction steps are simple and the yield is high.

Description

technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a preparation method of furan compounds. Background technique [0002] Furan is a very important heterocyclic unit that widely exists in natural and biologically important molecules. Multi-substituted furans play an important role in organic chemistry and are often used as building blocks in materials science and organic synthesis. For this reason, the synthesis of polysubstituted furans has attracted the interest of many chemists. [0003] In 2002, Vladimir Gevorgyan discovered a method using 1-phenylhept-2-yn-1-one as raw material, cuprous iodide as catalyst, triethylamine as base, and N,N-dimethylacetamide as Solvent, react at 100 degrees Celsius for 16 hours to synthesize furan compounds (Journal of Organic Chemistry, 67(1), 95-98; 2002). However, this method has the disadvantages that the reaction temperature is relatively high and the required time is relatively ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/36C07D307/38C07D307/42C07D307/58
CPCC07D307/36C07D307/38C07D307/42C07D307/58
Inventor 刘运奎胡晓君周丙伟
Owner ZHEJIANG UNIV OF TECH
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