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Method for preparing alcohol compound by utilizing lithium anilide compound as catalyst

A technology of lithium anilide and alcohol compound is applied in the application field of synthesis and preparation of alcohol compound, which can solve the problems of high safety risk, difficult catalyst and high cost, and achieve the effects of high reaction yield, simple post-processing and short reaction time.

Active Publication Date: 2021-01-01
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Existing hydroboration methods have significant disadvantages: LiAlH 4 and NaBH 4 The system security risk is very high, SmI 2 -H 2 O-Et 3 The N system needs a lot of reagents in excess, and the transition metal complex system needs to be carried out under high temperature and high pressure. On the one hand, it needs to use a catalyst that is difficult to synthesize, and the cost is high; on the other hand, the catalytic reaction requires 60 o The reaction temperature of C and the reaction time of 24 hours

Method used

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  • Method for preparing alcohol compound by utilizing lithium anilide compound as catalyst
  • Method for preparing alcohol compound by utilizing lithium anilide compound as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment one: Lithium anilide catalyzes the hydroboration reaction of benzoic acid and pinacol borane

[0025] Under an inert gas atmosphere, add benzoic acid (61.1 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and finally add 40 μl Tetrahydrofuran solution (0.1M) of lithium anilide (0.8 mol%, the same below), react at room temperature for 75 minutes, expose the reaction solution to air, remove the solvent, and obtain the product borate. Oxybenzene (84.15 mg, 0.5 mmol) was used as internal standard, and CDCl 3 Dissolve and stir for 10 minutes. Calculated 1 The yield of H is 99%; if the anilinolithium compound is replaced by the triaryloxy rare earth catalyst Nd(OAr) 3 (THF) 2 , no product is obtained. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) : δ 7.22– 7.32 (m, 5H, ArH), 4.92 (s, 2H, CH 2 ), 1.26 (s, 36H, CH 3 ).

[0026] Add 1g of silica gel and 3mL of met...

Embodiment 2

[0031] Embodiment 2: Lithium anilide catalyzes the hydroboration reaction of 4-fluorobenzoic acid and pinacol borane

[0032] Under an inert gas atmosphere, add 4-fluorobenzoic acid (70.8 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (290 μL, 2 mmol) with a pipette gun, and finally add The tetrahydrofuran solution of anilinolithium compound (0.8 mol% dosage) was reacted at room temperature for 75 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, which was sampled, and NMR was calculated. 1 H yield was 90%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 7.21 (br s, 2H, ArCH), 6.91 (t, 2H, ArCH), 4.75 (s, 2H, OCH 2 ), 1.15 (s,36H, CH 3). Add 1 g of silica gel and 3 mL of methanol to the system in which the solvent was removed after the hydroboration reaction, and react at 50°C for 135 minutes. After the reaction, extract three times with ethyl acetate, ...

Embodiment 3

[0033] Embodiment three: Lithium p-methylanilide catalyzes the hydroboration reaction of 4-bromobenzoic acid and pinacol borane

[0034] Under an inert gas atmosphere, add 4-bromobenzoic acid (100 mg, 0.5 mmol) to the reaction flask after dehydration and deoxygenation treatment, add pinacol borane (289 μL, 2 mmol) with a pipette gun, and finally add p- A tetrahydrofuran solution of lithium methylanilide (0.8 mol% dosage) was reacted at room temperature for 75 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, which was sampled and NMR was prepared. Calculated 1 H yield was 92%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ7.40 (br s, 2H, ArCH), 7.17 (t, 2H, ArCH), 4.81 (s, 2H, OCH 2 ), 1.20 (s, 36H,CH 3 ). Add 1 g of silica gel and 3 mL of methanol to the system in which the solvent was removed after the hydroboration reaction, and react at 50°C for 135 minutes. After the reaction, extract three times wit...

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Abstract

The invention relates to an application of an anilino lithium compound, in particular to a method for preparing an alcoholic compound from the anilino lithium compound as a catalyst. The catalyst, borane and carboxylic acid are stirred and mixed uniformly, subjected to a reaction and exposed to air to terminate the reaction, a reacted liquid is subjected to reduced-pressure treatment for solvent removal, silica gel and methanol are added, and the alcoholic compound is obtained by hydrolysis. The anilino lithium compound can perform high-activity catalysis on the reaction between carboxylic acid and borane at room temperature, dose of the catalyst is only 0.8mol% of the mole ratio of carboxylic acid, compared with the conventional catalysis system, the commercial reagent anilino lithium compound is used, reaction conditions are mild, and yield of borate with different substituents under limit conditions can reach 90% or higher.

Description

technical field [0001] The invention relates to the application of the commercialized reagent anilinolithium compound, in particular to the application of the anilinolithium compound to catalyze the synthesis of carboxylic acid and borane so as to prepare the alcohol compound. Background technique [0002] Alcohol compounds are common organic compounds with many uses and clear effects. There are various methods for preparing alcohol compounds, among which organic borates can be regarded as orthoboric acid B(OH) 3 It is an effective method for the synthesis of alcohol compounds. [0003] Existing hydroboration methods have significant disadvantages: LiAlH 4 and NaBH 4 The system security risk is very high, SmI 2 -H 2 O-Et 3 The N system needs a lot of reagents in excess, and the transition metal complex system needs to be carried out under high temperature and high pressure. On the one hand, it needs to use a catalyst that is difficult to synthesize, and the cost is high...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/04C07C29/12C07C33/22B01J31/02
CPCB01J31/0252C07C29/12C07F5/04C07C33/22
Inventor 薛明强徐晓娟颜丹丹陈素芳蔡玲霞沈琪
Owner SUZHOU UNIV
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