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A kind of method of simply synthesizing propynyl alcohol

A kind of propynyl alcohol, simple technology, applied in the field of preparation of propynyl alcohol, can solve the problems of inconvenient operation, harsh reaction conditions, etc., and achieve the effect of convenient operation, short reaction cycle and mild reaction conditions

Active Publication Date: 2016-08-17
CHENGDU ZHIPULAI BIOMEDICINE TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, metal reagents such as alkylzinc and butyllithium are extremely sensitive to water, and the water content of the reaction system needs to be strictly controlled. The reagents, solvents, and utensils required for the reaction must be strictly dried without water, so the reaction conditions are harsh and the operation is inconvenient.

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  • A kind of method of simply synthesizing propynyl alcohol

Examples

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Effect test

Embodiment 1

[0026] A kind of method of simply synthesizing propynyl alcohol, be phenylacetylene p-methyl benzoylformate addition reaction in the present embodiment, concrete operation steps are as follows:

[0027] In the atmosphere, add activated zinc powder (3 mmol, 6 equiv), MeI (6 mmol, 12 equiv), phenylacetylene (2 mmol, 4 equiv), 0.5ml N-methylpyrrolidone to a 25ml round bottom flask, and stir at room temperature 2h, until the activated zinc powder disappears.

[0028] After the zinc dust disappeared completely, a dichloromethane solution of methyl benzoylformate (0.5 mmol, 1 equiv) was added, and the reaction process was monitored by silica gel thin-layer chromatography, stirred at room temperature for 12 h, the raw material methyl benzoylformate disappeared, and the reaction was stopped. Add 10ml of saturated ammonium chloride aqueous solution and dichloromethane to the reaction solution, stir for 10min, separate the organic phase, extract the aqueous phase with dichloromethane th...

Embodiment 2

[0032] In this example, the addition reaction of phenylacetylene to α, α, α-trifluoroacetophenone, the specific operation steps are as follows:

[0033] In the atmosphere, add activated zinc powder (3 mmol, 6 equiv), MeI (6 mmol, 12 equiv), phenylacetylene (2 mmol, 4 equiv), 0.5 ml N-methylpyrrolidone into a 25ml round bottom flask, stir at room temperature 2h, until the zinc powder disappears.

[0034] After the zinc powder disappeared completely, a dichloromethane solution of α,α,α-trifluoroacetophenone (0.5 mmol, 1 equiv) was added, and the reaction progress was monitored by silica gel thin-layer chromatography, and stirred at room temperature for 12 hours. The raw materials α,α,α- Trifluoroacetophenone disappears, stop reaction, add 10ml saturated ammonium chloride aqueous solution and dichloromethane to reaction liquid, stir 10min, separate organic phase, water phase is extracted three times with dichloromethane, combine organic phase, wash with saturated saline, Dry ove...

Embodiment 3

[0038] Be phenylacetylene to benzaldehyde addition reaction in the present embodiment, concrete operating steps are as follows:

[0039] In the atmosphere, add activated zinc powder (3 mmol, 6 equiv), MeI (6 mmol, 12 equiv), phenylacetylene (2 mmol, 4 equiv), 0.5 ml N-methylpyrrolidone into a 25ml round bottom flask, and stir at room temperature for 2h , until the activated zinc powder disappears.

[0040] After the zinc powder disappeared completely, add a dichloromethane solution of benzaldehyde (0.5 mmol, 1 equiv), monitor the reaction process by silica gel thin-layer chromatography, stir at room temperature for 12 hours, the raw material benzaldehyde disappeared, stop the reaction, and add 10 ml of saturated chlorine to the reaction solution. Ammonium chloride aqueous solution and dichloromethane were stirred for 10 minutes, the organic phase was separated, the aqueous phase was extracted three times with dichloromethane, the organic phases were combined, washed with satur...

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Abstract

The invention discloses a method for synthesizing propiolic alcohol in a simple mode. The method solves the problems of extreme sensitivity on water and air in a traditional method and difficult realization on massive production in prior art. The method comprises the following steps: 1)adding activated zinc powder, iodomethane or iodoethane, terminal acetylene, and a solvent in a reaction container; stirring at room temperature until the zinc powder disappears; 2)after the zinc powder is completely disappeared, adding a carbonyl compound dissolved by an organic solvent; and 3)stirring at room temperature and stopping the reaction until the carbonyl compound disappears, and separating a reaction solution and purifying to obtain the product. The method has the advantages of mild reaction condition, easily available raw materials, convenient operation, short reaction period and large scale production.

Description

technical field [0001] The invention relates to a preparation method of propynyl alcohol, in particular to the addition reaction of terminal alkynes to carbonyl compounds. Background technique [0002] Proynyl alcohol is an important intermediate in organic synthesis. On the one hand, it is widely used in the synthesis of natural products, drugs, and complex macromolecular compounds; on the other hand, two flexible functional groups, alkynyl and hydroxyl, can be converted It has great potential application value in molecular diversity. [0003] Proynyl alcohol can be prepared by the addition reaction of terminal alkynes to aldehydes or ketones. The reaction process is generally through the reaction of active metal reagents such as alkyl zinc and butyl lithium with terminal alkynes to generate alkynyl zinc or alkynyl lithium reagents. , and then add to the carbonyl compound to obtain the propynyl alcohol compound. However, metal reagents such as alkylzinc and butyllithium a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/347C07C69/732C07C29/42C07C33/28C07C33/48C07C33/34
CPCC07C29/42C07C33/28C07C33/34C07C33/48C07C67/347C07C69/732
Inventor 陈伟张文赵刚蒲林刘继峰
Owner CHENGDU ZHIPULAI BIOMEDICINE TECH CO LTD
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