Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Method for preparing boric acid ester based on hydroboration reaction of aliphatic carboxylic acid

An aliphatic carboxylic acid and hydroboration technology, which is applied in catalytic reactions, chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, etc., can solve the problem of high cost, and achieve short reaction time and high yield. , the effect of mild reaction conditions

Active Publication Date: 2020-07-14
SUZHOU UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the one hand, the existing method 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

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
  • Method for preparing boric acid ester based on hydroboration reaction of aliphatic carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: N-butyllithium catalyzes the hydroboration reaction of acetic acid and pinacol borane

[0023] Under an inert gas atmosphere, add acetic acid (28.6 μL, 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 10 μL n-butyl Lithium tetrahydrofuran solution (0.1M) (0.2 mol% dosage, the same below), reacted at room temperature for 15 minutes, exposed the reaction solution to air, and removed the solvent to obtain the product boric acid ester, which was obtained by s-trimethoxybenzene (84.08 mg , 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 99%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ3.88 (q, 2H, CH 2 ), 1.25 (s, 36H, CH 3 ), 1.21 (br s, 3H, CH 3 ).

[0024] When pinacol borane (218 μL, 1.5 mmol), the yield was 95%; when pinacol borane (363 μL, 2.5 mmol), the yield was...

Embodiment 2

[0025] Example 2: n-Butyl Lithium Catalyzed Hydroboration Reaction of Valeric Acid and Pinacol Borane

[0026] Under an inert gas atmosphere, add valeric acid (54.38 μL, 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 n-butyl The tetrahydrofuran solution of lithium (0.2 mol% dosage) was reacted at room temperature for 15 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (84.12 mg, 0.5 mmol) as internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 92%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.81 (t, 2H,OCH 2 ), 1.52-1.56 (m, 2H,CH 2 ), 1.30-1.52 (m, 4H, CH 2 ), 1.28(s, 36H, CH), 0.86(t, 3H, CH 3 ).

Embodiment 3

[0027] Embodiment 3: n-Butyllithium catalyzes the hydroboration reaction of hexanoic acid and pinacol borane

[0028] Under an inert gas atmosphere, add hexanoic acid (62.52 μL, 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 n-butyl The tetrahydrofuran solution of lithium (0.2 mol% dosage) was reacted at room temperature for 15 minutes, the reaction solution was exposed to air, and the solvent was removed to obtain the product borate, with s-trimethoxybenzene (84.01 mg, 0.5 mmol) as the internal standard, with CDCl 3 Dissolved, stirred for 10 minutes, sampled, and NMR. Calculated 1 H yield was 90%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ): δ 3.76 (t, 2H,OCH 2 ), 1.46-1.52 (m, 2H,CH 2 ), 1.24-1.35 (m, 6H, CH 2 ), 1.19 (s, 48H, CH 3 ), 0.82(t, 3H, CH 3 ).

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 relates to an application of n-butyllithium in catalysis of a hydroboration reaction of aliphatic carboxylic acid and borane. A catalyst, the borane and the carboxylic acid are uniformlystirred and mixed, and reacted for 10-20 minutes, the reaction is terminated by exposing in air, and a solvent is removed through vacuum distillation of the reaction solution to obtain borate with different substituent groups. The n-butyllithium disclosed by the invention can catalyze the hydroboration reaction of carboxylic acid and borane with high activity at room temperature, and the catalystadopted is 0.2 mol% of the carboxylic acid. Compared with the existing catalytic system, the commercial reagent n-butyllithium has advantages of mild reaction condition is mild and capability of enabling the yield of borate with different substituent groups to reach 99% under the limited condition.

Description

technical field [0001] The application of the commercialized reagent n-butyllithium involved in the present invention, in particular, relates to a method for preparing boric acid ester based on hydroboration reaction of aliphatic carboxylic acid. Background technique [0002] Due to its stability and low toxicity, borate is widely used in various fields, and it is a main raw material for the synthesis of boron-containing compounds. On the one hand, the existing method 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 C reaction temperature and 24 hours reaction time. The difference between carboxylic acid and aldehyde and ketone nucleophilic addition reaction activity: (1) The active hydrogen of carboxylic acid is easy to leave, so its two Os are actually equivalent, so from the perspective of space structure, the steric hindrance of carboxyl group is relatively small. Large, and the prese...

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): C07F5/04
CPCB01J31/122B01J2231/42C07F5/04
Inventor 薛明强颜丹丹徐晓娟康子晗洪玉标沈琪
Owner SUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com