A novel compound 6,6-dimethyltetrahydropyran-2-methanol and its preparation method

A technology of dimethyltetrahydropyran and compounds, which is applied in the direction of organic chemistry, can solve the problems of long steps, expensive raw materials, and difficult synthesis of pyranylmethanol compounds, and achieve the effect of mild reaction, easy handling and purification

Inactive Publication Date: 2020-02-11
HENAN VOCATIONAL & TECHN COLLEGE OF COMM
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, pyranylcarbinyl compounds are not easy to synthesize, and the general preparation methods mostly have long steps, expensive raw materials, difficult operation and low yield, which greatly limits the efficient preparation and application requirements of pyranylcarbinol compounds.

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation method of the 6,6-dimethyltetrahydropyran-2-methanol of the present embodiment is as follows:

[0028] (1) Synthesis of benzyloxyethanol 1

[0029] 2.3 g (0.1 mol) of sodium was added to a solution of 30 g (0.5 mol) of ethylene glycol in tetrahydrofuran (100 mL), and the temperature was controlled at 50°C. After the resulting mixture was stirred under reflux for 0.5 hours, 17.1 g (0.1 mol) of benzyl bromide was added dropwise, followed by reflux overnight. The next day, 100 mL of water was added, most of the solvent was removed by a rotary evaporator, and then 80 mL of ethyl acetate was added to separate the organic phase, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated, which was purified by distillation, collecting fractions at 70°C (2 mmHg) to give 12.1 g of product, yield 80%.

[0030] MS: m / z: [M+Na] + :176;

[0031] 1 H ...

Embodiment 2

[0053] The preparation method of the 6,6-dimethyltetrahydropyran-2-methanol of the present embodiment is as follows:

[0054] (1) Synthesis of benzyloxyethanol 1

[0055] Add 31.6 g (0.51 mol) of ethylene glycol into a tetrahydrofuran (100 mL) solution, then add 2.53 g (0.11 mol) of sodium, and control the temperature at 50°C. Then the resulting mixture was stirred under reflux for 0.5 hour, 17.1 g (0.1 mol) of benzyl bromide was added dropwise, and the mixture was refluxed overnight. Then 100 mL of water was added, and most of the solvent was removed by a rotary evaporator, and then 80 mL of ethyl acetate was added, the organic phase was separated, and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated. They were purified by distillation and collected fractions at 70°C (2 mmHg) to give 12.4 g of product, yield 82%.

[0056] (2) Synthesis of benzyloxyacetaldehyde...

Embodiment 3

[0067] The preparation method of the 6,6-dimethyltetrahydropyran-2-methanol of the present embodiment is as follows:

[0068] (1) Synthesis of benzyloxyethanol 1

[0069] Add 32.8 g (0.53 mol) of ethylene glycol into a tetrahydrofuran (100 mL) solution, then add 3.0 g (0.13 mol) of sodium, and control the temperature at 50°C. Then the resulting mixture was stirred under reflux for 0.5 hour, 17.1 g (0.1 mol) of benzyl bromide was added dropwise, and the mixture was refluxed overnight. Then 100 mL of water was added, and most of the solvent was removed by a rotary evaporator, and then 80 mL of ethyl acetate was added, the organic phase was separated, and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated. They were purified by distillation and collected fractions at 70°C (2mmHg) to give 12.86g of product, yield 85%.

[0070] (2) Synthesis of benzyloxyacetaldehyde 2...

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 discloses a novel compound that is 6,6-dimethyl tetrahydropyran-2-methanol and a preparing method thereof. The method includes preparing benzyloxy ethanol by utilizing a sodium alkoxideprocess; then oxidizing the benzyloxy ethanol into benzyloxy acetaldehyde by utilizing a swern oxidation process; reacting the benzyloxy acetaldehyde and allyltributyltin prepared by utilizing a Grignard reaction to obtain 1-(benzyloxy)-4-penten-2-ol; subjecting the 1-(benzyloxy)-4-penten-2-ol and acetone to cyclization under catalysis of trimethylchlorosilane and potassium iodide to obtain 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol; and subjecting the 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol to hydrogenation to remove iodine to obtain the target product that is the 6,6-dimethyl tetrahydropyran-2-methanol. According to the method, reactions are relatively mild, products can be easily treated and purified, and the method is suitable for batch preparation, and therefore the methodhas important application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a novel compound 6,6-dimethyltetrahydropyran-2-methanol and a preparation method thereof. Background technique [0002] Pyranylcarbinyl compounds have very diverse uses, and this structure has good pharmacological activity. Some drugs for the treatment of hypertension and drugs for the treatment of cardiovascular and nervous system degenerative diseases contain pyranylcarbinyl structures or fragments. Methanol also exists in many natural product molecules, so pyranylmethanol derivatives are important organic and pharmaceutical intermediates. However, pyranylcarbinyl compounds are not easy to synthesize, and the general preparation methods mostly have long steps, expensive raw materials, difficult operation and low yields, which greatly limit the efficient preparation and application requirements of pyranylcarbinol compounds. In particular, there are few repo...

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): C07D309/06
CPCC07D309/06
Inventor 张永霞梁庚靳清贤李争光
Owner HENAN VOCATIONAL & TECHN COLLEGE OF COMM
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
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap