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Preparation method of beta, gamma-unsaturated ester compound

An ester compound and unsaturated technology, applied in the beta field, can solve the problems of unsuitability for industrial production and application, long reaction time, etc., and achieve the effects of mild reaction conditions, low price and high yield

Active Publication Date: 2017-06-27
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This reaction is carried out under the condition of visible light, needs to use expensive photocatalyst terpyridyl ruthenium chloride, and the catalytic system also needs to be carried out under the condition of alkali and various organic additives, and the reaction time is too long, so it is not suitable for industrial production application ( See prior art document 2: Visible-LightPhotocatalytic Radical Alkenylation ofα-Carbonyl Alkyl Bromides and Benzyl Bromides, Chem.Eur.J.2013, 19, 5120-5126)

Method used

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  • Preparation method of beta, gamma-unsaturated ester compound
  • Preparation method of beta, gamma-unsaturated ester compound
  • Preparation method of beta, gamma-unsaturated ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 72.0 mg (0.4 mmol) of 1,1-diphenylethylene, 99.6 mg (0.6 mmol) of methyl 2-bromopropionate, 9.3 mg (0.04 mmol) of silver oxide, and tert-butyl peroxide into a dry 10 mL schlenk bottle. Alcohol 72.0mg (0.8mmol), triethylamine 80.8mg (0.8mmol), N,N-dimethylacetamide (2mL), and the reaction bottle was stirred at 80°C under an argon atmosphere for 24h. After the reaction was completed, the reaction solution was washed with saturated brine, extracted with ethyl acetate (3×10 mL), and the organic phase was collected and dried by adding anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate) to obtain the target product (2-methyl-4,4-diphenylbut-3-enoic acid methyl ester), yellow Oily liquid, yield 92%. 1 H NMR (400MHz, CDCl 3 ) δ: 7.40-7.32(m, 3H), 7.25-7.19(m, 7H), 6.12(d, J=10.4Hz, 1H), 3.67(s, 3H), 3.32-3.28(m, 1H), 1.27 (d, J=6.8Hz, 3H); 13...

Embodiment 2

[0027] Add 72.0 mg (0.4 mmol) of 1,1-diphenylethylene, 99.6 mg (0.6 mmol) of methyl 2-bromopropionate, 11 mg (0.04 mmol) of silver carbonate, and tert-butanol peroxide into a dry 10 mL schlenk bottle 72.0mg (0.8mmol), 80.8mg (0.8mmol) of triethylamine, N,N-dimethylacetamide (2mL), and the reaction bottle was stirred at 80°C under an argon atmosphere for 24h. After the reaction was completed, the reaction solution was washed with saturated brine, extracted with ethyl acetate (3×10 mL), and the organic phase was collected and dried by adding anhydrous magnesium sulfate. The organic solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography (petroleum ether / ethyl acetate) to obtain the target product (2-methyl-4,4-diphenylbut-3-enoic acid methyl ester). rate of 85%.

Embodiment 3

[0029] Proceed according to the method of Example 1, wherein the difference is that 117 mg (0.8 mmol) of DTBP is added to replace the butanol peroxide to obtain a target product yield of 15%.

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Abstract

The invention discloses a preparation method of beta, gamma-unsaturated ester. A structural formula of the beta, gamma-unsaturated ester is shown in the description. The preparation method of the beta, gamma-unsaturated ester comprises the following steps: adding 1,1-diphenylethlene and 2-bromopropionate into a reaction system containing a silver catalyst, an oxidant, alkali and a solvent for reacting.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of β, γ-unsaturated ester compounds. Background technique [0002] β, γ-unsaturated esters are an important class of intermediates in organic synthesis. In recent years, chemists are devoting themselves to the research of new methods for the synthesis of β, γ-unsaturated esters. [0003] In 2012, Lei Aiwen et al. reported a nickel-catalyzed Heck-Type alkenylation reaction of α-carbonylalkyl bromide (see equation 1). The reaction needs to be carried out under the conditions of nickel tetraphenylphosphine as a catalyst, dppp as a ligand and potassium phosphate as a base. It has good substrate adaptability and yield, and a series of β, γ-unsaturated esters have been synthesized. (See prior art document 1: Nickel-Catalyzed Heck-Type Alkenylation of Secondary and Tertiary a-Carbonyl Alkyl Bromides, Angew. Chem. Int. Ed. 2012, 51, 3638-3641). [0004...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C69/618
CPCC07C67/343C07C69/618
Inventor 黄会燕魏文廷朱文明应炜炜赵船丽杨晨光陈卫东
Owner NINGBO UNIV
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