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Method for preparing propargyl alcohol compound by taking pinacol borane as hydrogen source

A technology of pinacol borane and propargyl alcohol, applied in the field of chemistry, can solve the problems of unsatisfactory substrate applicability and poor functional group tolerance, and achieve simple method, mild reaction conditions and strong atom economy. Effect

Pending Publication Date: 2022-04-29
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of reaction usually generates an alkynyl intermediate by reacting a strong base with the terminal hydrogen of a terminal alkyne, but the addition of a strong base usually makes other functional groups less tolerant
Although a class of catalytic alkynylation reactions has been developed in recent years, it is still unsatisfactory in terms of substrate suitability.

Method used

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  • Method for preparing propargyl alcohol compound by taking pinacol borane as hydrogen source
  • Method for preparing propargyl alcohol compound by taking pinacol borane as hydrogen source
  • Method for preparing propargyl alcohol compound by taking pinacol borane as hydrogen source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Preparation of 4-phenyl-3-butyn-2-ol

[0042]

[0043] In a water-free and oxygen-free glove box under argon atmosphere 4 NBr (0.02 mmol) was added to a 10 mL reaction tube, then 2 ml THF (tetrahydrofuran), then pinacol borane (1.0 mmol) was sent out of the glove box, and then 4-phenyl-3-butyne- 2-Keto (0.2 mmol). Reaction in 60°C oil bath, TLC monitoring and I 2 The reaction was detected by color development. After the reaction was completed, it was quenched by adding sodium hydroxide solution (15mol / L), extracted and concentrated, and carried out silica gel column chromatography with petroleum ether / ethyl acetate as eluent to obtain 4-phenyl-3 -butyn-2-ol. Yellow oily liquid, yield 94%. 1 HNMR (400MHz, CDCI 3 ) 7.44-7.41, (m, 2H), 7.31-7.29 (m, 2H), 4.78-4.73 (m, 1H), 1.56-1.54 (m, 1H).

Embodiment 2

[0044] Example 2 Preparation of (2-methylphenyl)-3-butyn-2-alcohol

[0045]

[0046] In a water-free and oxygen-free glove box under argon atmosphere 4 NBr (0.02 mmol) was added to a 10 mL reaction tube, then 2 ml THF (tetrahydrofuran), then pinacol borane (1.0 mmol) was sent out of the glove box, and then (2-methylphenyl)-3 -butyn-2-one (0.2 mmol). Reaction in 60°C oil bath, TLC monitoring and I 2 The reaction was detected by color development. After the reaction was completed, it was quenched by adding sodium hydroxide solution (15mol / L), extracted and concentrated, and carried out silica gel column chromatography with petroleum ether / ethyl acetate as eluent to obtain (2-methylbenzene base)-3-butyn-2-ol. Yellow oily liquid, yield 80%. 1 H NMR (400MHz, CDCI 3) 7.40-7.38 (d, 1H), 7.26-7.10 (m, 3H), 4.82-4.77 (m, 1H), 2.42 (s, 3H), 1.58-1.56 (d, 3H).

Embodiment 3

[0047] Example 3 Preparation of 4-(2-fluorophenyl)-3-butyn-2-ol

[0048]

[0049] In an anhydrous and oxygen-free glove box under argon atmosphere 4 NBr (0.02 mmol) was added to a 10 mL reaction tube, then 2 ml THF (tetrahydrofuran), then pinacol borane (1.0 mmol) was sent out of the glove box, and then 4-(2-fluorophenyl)- 3-Butyn-2-one (0.2 mmol). Reaction in 60°C oil bath, TLC monitoring and I 2 The reaction was detected by color development. After the reaction was completed, it was quenched by adding sodium hydroxide solution (15mol / L), extracted and concentrated, and carried out silica gel column chromatography with petroleum ether / ethyl acetate as eluent to obtain 4-(2-fluoro Phenyl)-3-butyn-2-ol. Yellow oily liquid, yield 55%. 1H NMR(400MHz, CDCI3)δ7.44-7.39(m,1H), 7.33-7.26(m,1H), 7.11-7.04(m,2H), 4.82-4.77(m,1H), 1.58-1.57(d ,3H).

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Abstract

The invention discloses a method for preparing propargyl alcohol compounds by taking pinacol borane as a hydrogen source, which comprises the following steps: by taking alkyne acetone as a reaction substrate, dissolving a catalyst and pinacol borane in a dry organic solvent in a reaction tube, then adding the reaction substrate, reacting at the temperature of 40-70 DEG C until the substrate is completely consumed, then adding a sodium hydroxide solution for quenching, and separating and purifying to obtain the propargyl alcohol compounds. And after extraction and concentration, purifying by silica gel column chromatography to obtain the propargyl alcohol compound. According to the method, pinacol borane is used as a hydrogen source to catalyze the acetylenic acetone compound to generate the propargyl alcohol compound, and the yield is as high as 94%. According to the preparation method, the quaternary ammonium salt which is cheap and easy to obtain is used as the catalyst, metal does not need to be added, and reaction conditions are mild. In addition, reagents used in the preparation method are cheap and easy to obtain, and the method is simple, convenient to operate, high in atom economy and suitable for conventional preparation.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a method for preparing propargyl alcohol compounds by using pinacol borane as a hydrogen source. Background technique [0002] Propargyl alcohol compounds are very important intermediates in organic synthesis because they contain both acetylenic bonds and hydroxyl groups. Through research in recent years, it has been found that it has a wide range of application values ​​in medicine, synthetic materials, polymers, petroleum, etc. In addition, it shows strong excellent performance in surface activity, dispersibility, and slow-release performance. Propargyl alcohol compounds are also important intermediates in the synthesis of some anticancer and antineoplastic drugs. Although natural products with propargyl alcohol compound structures have received extensive attention, the content of propargyl alcohol-containing compounds in natural medicinal materials is extremely ...

Claims

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Application Information

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IPC IPC(8): C07C29/143C07C33/30C07C33/48
CPCC07C29/143C07C33/30C07C33/483
Inventor 樊保敏陈景超周永云和振秀樊瑞峰孙蔚青周宾斌
Owner YUNNAN MINZU UNIV
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