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Preparation method of alkyl nitrile compound

A compound, the technology of alkyl nitriles, applied in the field of preparation of alkyl nitriles, can solve the problems of poor compatibility of universal functional groups of substrates, poor efficiency and selectivity of hydrocyanation reaction, and easy volatility

Active Publication Date: 2020-08-04
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0038] The technical problem to be solved by the present invention is to overcome that the cyanation reagent hydrogen cyanide used in the existing nickel-catalyzed olefin hydrocyanation reaction is highly toxic and volatile, has poor substrate universality and functional group compatibility, and is non-activated. The efficiency and selectivity of the hydrocyanation reaction of alkyl olefins are relatively poor, and a kind of preparation method of alkyl nitrile compound is provided

Method used

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  • Preparation method of alkyl nitrile compound
  • Preparation method of alkyl nitrile compound
  • Preparation method of alkyl nitrile compound

Examples

Experimental program
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preparation Embodiment 1

[0111]

[0112] Under argon protection, methyltriphenylphosphine bromide (2.14g, 6mmol) was dissolved in dry tetrahydrofuran (10ml), and KO was added thereto t Bu (785.5 mg, 7 mmol). The reaction solution was stirred at room temperature for 30 minutes and then cooled to -78°C. A solution of 3,5-dimethoxybenzaldehyde (830.9 mg, 5 mmol) in tetrahydrofuran (5 mL) was added dropwise thereto, and after the addition, the reaction returned to room temperature and continued to stir for 12 h. The reaction was quenched by adding 2 mL of methanol, and the reaction solution was concentrated and purified by silica gel column chromatography. Eluent: petroleum ether / ethyl acetate=10:1, the product is 811mg of colorless liquid, the yield is 99%, 1 H NMR purity greater than 98%. 1 H NMR (400M, CDCl 3 ):δ3.79(s,6H),5.24(d,J=10.8Hz,1H),5.72(dd,J=17.6,0.8Hz,1H),6.38(t,J=2.4Hz,1H),6.56 (d,J=2.4Hz,2H),6.64(dd,J=17.6,10.8Hz,1H). 13 C NMR (100M, CDCl 3 ): δ55.23, 99.97, 104.20, 114.27, 136....

preparation Embodiment 2

[0114]

[0115] Under argon protection, methyltriphenylphosphine bromide (1.7861g, 5mmol) was dissolved in dry tetrahydrofuran (25mL) and cooled to 0°C, and added n BuLi (2 mL, 2.5M in hexane, 5 mmol) and stirring was continued at this temperature for 2 h. A solution of benzothiophene-2-carbaldehyde (811.1 mg, 5 mmol) in tetrahydrofuran (4 mL) was continuously added thereto. The reaction solution was returned to room temperature and continued to stir for 4 h, and then quenched with water. After extraction with ether, wash with water and saturated NaCl, anhydrous Na 2 SO 4 Dry, concentrate by filtration, and purify by silica gel column chromatography. Eluent: petroleum ether / ethyl acetate=10:1, the product is 665mg of white solid, yield 83%, 1 H NMR purity greater than 98%. 1 H NMR (400M, CDCl 3 ):δ5.28(d,J=10.8Hz,1H),5.65(d,J=17.2Hz,1H),6.89(dd,J=17.2,10.8Hz,1H),7.13(s,1H),7.25 -7.31(m,2H),7.65-7.67(m,1H),7.73-7.75(m,1H). 13 C NMR (100M, CDCl 3 ): δ115.89, 122.21, ...

preparation Embodiment 3

[0117]

[0118] Under the protection of argon, formononetin (2.68g, 10mmol) and triethylamine (2.02g, 20mmol) were dissolved in dichloromethane (50mL), and Tf was added thereto after cooling to 0°C 2 O (3.10g, 11mmol), return to room temperature and react for 2h after addition. with saturated NH 4 The reaction was quenched with Cl and extracted with dichloromethane. After combining the organic phases with anhydrous Na 2 SO 4 After drying, filtration and concentration, column chromatography purification, eluent: petroleum ether / dichloromethane=1:2, the intermediate trifluoromethanesulfonyl-protected formononetin was obtained, the product was a white solid 2.76g, the yield 69%, 1 H NMR purity greater than 98%. 1 H NMR (400M, CDCl 3 ):δ3.84(s,3H),6.97(d,J=8.8Hz,2H),7.33(dd,J=8.8,2.4Hz,1H),7.45(d,J=2.0Hz,1H),7.49 (d,J=8.8Hz,2H),8.01(s,1H),8.40(d,J=8.8Hz,1H). 13 C NMR (100M, CDCl 3 ):δ55.26, 111.39, 114.04, 118.47, 118.63 (q, 1 J C-F=321.3Hz), 123.08, 124.14, 125.62, ...

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Abstract

The invention discloses a preparation method of an alkyl nitrile compound. Specifically, the preparation method comprises the following step: in an organic solvent, in the presence of a protective gasand under the action of a catalyst, carrying out a reduction reaction as shown in the specification on olefin as shown in a formula I, a cyanation reagent and water, wherein the alkyl nitrile compound 1 is a compound II and / or a compound III. The preparation method provided by the invention is mild in condition, can realize hydrocyanation of olefin more safely and efficiently, and has good substrate universality and functional group compatibility.

Description

technical field [0001] The invention relates to a preparation method of alkyl nitrile compounds. Background technique [0002] Nitrile compounds are widely distributed in medicines, pesticides, functional materials and molecules with biological activity. For example, acetonitrile, as the nitrile compound with the smallest molecular weight, is often used as a solvent for organic reactions. Acrylonitrile is often used as a polymer monomer, and plays an important role in synthetic fibers, resins, rubber and other polymer materials. Halogen-containing aryl nitriles such as bromoxynil and ioxynil are commonly used as insecticides. Ricinine produced in microorganisms and plants also contains cyano functional groups. Many nitriles and their derivatives have been found to have high drug activity, such as anti-inflammatory, anti-inflammatory, analgesic ibuprofen and Napson are derivatives corresponding to benzonitrile, cyano-containing western medicine vildagliptin, Saxagliptin i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36C07C41/30C07C43/215C07D333/54C07J1/00C07C29/40C07C33/30C07C253/10C07C255/33C07C255/37C07C255/36C07C255/42C07C255/35C07F7/18C07F5/02C07D213/57C07D209/18C07D333/60C07D207/27C07D209/86C07D209/48C07C255/31
CPCC07D311/36C07C41/30C07C43/215C07D333/54C07J1/0059C07C29/40C07C33/30C07C253/10C07C255/33C07C255/37C07C255/36C07C255/42C07C255/35C07F5/025C07D213/57C07D209/18C07D333/60C07D207/27C07D209/86C07D209/48C07C255/31C07C2601/14Y02P20/55
Inventor 刘元红王高男解鑫
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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