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Method for synthesizing alpha-alkyl ketone

A technology of alkyl ketone and alkyl, which is applied in the field of synthesis of α-alkyl ketones, can solve the problems of waste salt and achieve broad development prospects

Inactive Publication Date: 2015-04-29
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires the use of toxic halogenated hydrocarbons and produces a large amount of waste salt

Method used

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  • Method for synthesizing alpha-alkyl ketone
  • Method for synthesizing alpha-alkyl ketone
  • Method for synthesizing alpha-alkyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: 1,3-diphenyl-1-propanone

[0027] 1,3-diphenylpropan-1-one

[0028]

[0029] [(IPr)AuCl] (6mg, 0.01mmol, 1mol%), AgOTf (2.6mg, 0.01mmol, 1mol%), phenylacetylene (102mg, 1mmol), 1,4-dioxane (1ml) and water (36ul, 2equiv.) were added to 5ml microwave tubes in turn. The reaction mixture was reacted in a microwave reactor at 120° C. for 1 hour, and then cooled to room temperature. Then add [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), potassium tert-butoxide (34mg, 0.3mmol, 0.3equiv.), benzyl alcohol (130mg, 1.2mmol). The reaction mixture was reacted in a microwave oven at 130° C. for another 2 hours, and then cooled to room temperature. Filtrate, remove the solvent by rotary evaporation, and then obtain the pure target compound by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 87%

[0030] 1 H NMR (500MHz, CDCl 3 )δ7.96(d,J=7.6Hz,2H,ArH),7.56(t,J=7.3Hz,1H,ArH),7.46(t,J=7.6Hz,2H,ArH),7.34-7.24(m ,4H,ArH),7.21(t,J=7.2Hz,1H,A...

Embodiment 2

[0031] Example 2: 3-(4-methylphenyl)-1-phenyl-1-propanone

[0032] 1-phenyl-3-p-tolylpropan-1-one

[0033]

[0034] [(IPr)AuCl] (6mg, 0.01mmol, 1mol%), AgOTf (2.6mg, 0.01mmol, 1mol%), phenylacetylene (102mg, 1mmol), 1,4-dioxane (1ml) and water (36ul, 2equiv.) were added to 5ml microwave tubes in turn. The reaction mixture was reacted in a microwave reactor at 120° C. for 1 hour, and then cooled to room temperature. Then add [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), potassium tert-butoxide (34mg, 0.3mmol, 0.3equiv.), 4-methylbenzyl alcohol (146mg, 1.2mmol). The reaction mixture was reacted in a microwave reactor at 130° C. for another 2 hours, and then cooled to room temperature. Filtrate, remove the solvent by rotary evaporation, and then obtain the pure target compound by column chromatography (developing solvent: petroleum ether / ethyl acetate), yield: 86%

[0035] 1 H NMR (500MHz, CDCl 3 )δ7.96(d,J=6.8Hz,2H,ArH),7.55(t,J=7.4Hz,1H,ArH),7.45(t,J=7.4Hz,2H,ArH),7.20-7.06...

Embodiment 3

[0036] Example 3: 3-(3,4-dimethylphenyl)-1-phenyl-1-propanone

[0037] 3-(3,4-dimethylphenyl)-1-phenylpropan-1-one

[0038]

[0039][(IPr)AuCl] (6mg, 0.01mmol, 1mol%), AgOTf (2.6mg, 0.01mmol, 1mol%), phenylacetylene (102mg, 1mmol), 1,4-dioxane (1ml) and water (36ul, 2equiv.) were added to 5ml microwave tubes in turn. The reaction mixture was reacted in a microwave reactor at 120° C. for 1 hour, and then cooled to room temperature. Then add [Cp*IrCl 2 ] 2 (8mg, 0.01mmol, 1mol%), potassium tert-butoxide (34mg, 0.3mmol, 0.3equiv.), 3,4-dimethylbenzyl alcohol (163mg, 1.2mmol). The reaction mixture was microwaved at 130°C for 2 hours and then cooled to room temperature. Filtration, rotary evaporation to remove the solvent, and then column chromatography (developing solvent: petroleum ether / ethyl acetate) to obtain the pure target compound, yield: 91%

[0040] 1 H NMR (500MHz, CDCl 3 )δ7.96(dd,J=8.4Hz and1.3Hz,2H,ArH),7.55(t,J=7.4Hz,1H,ArH),7.45(t,J=7.7Hz,2H,ArH),7.09- 6...

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Abstract

The invention discloses a method for synthesizing alpha-alkyl ketone. The method comprises the following steps: adding alkyne, [(IPr)AuCl], AgOTf, 1,4-dioxane and water in a reaction container, performing microwave reaction on a reaction mixture for 1h at 120 DEG C and cooling to room temperature; further adding [Cp*IrCl2]2, alkali and alcohol into the reaction mixture, performing microwave reaction on the reaction mixture for 2h at 130 DEG C and cooling to room temperature; filtering, performing rotary evaporation to remove a solvent, and then separating by a column to obtain a target compound. The method disclosed by the invention is started from chemical raw materials which are easy to obtain, namely alkyne, water and alcohol, alpha-alkyl ketone is obtained under the participation of gold and iridium catalysts, and the reaction only generates water as a byproduct. Therefore, the reaction is in line with the requirements of green chemistry and has broad development prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing α-alkyl ketones. Background technique [0002] α-Alkyl ketones are a very important class of compounds, exhibiting a wide range of physiological and pharmacological activities. For example, such compounds are used as reversible ketoheterocyclic inhibitors of fatty acid amide hydrolase (OL-135), thyroid receptor coactivator binding inhibitors, orally bioavailable phthalazinone bradykinin B1 receptors, body antagonists and 5-HT 7 receptor ligands, etc. (a) D. L. Boger, H. Miyauchi, W. Du, C. Hardouin, R. A. Fecik, H. Cheng, I. Hwang, M. P. Hedrick, D. Leung, O. Acevedo, C. R. W. W.L.Jorgensen, B.F.Cravatt, J.Med.Chem.2005,48,1849-1856; b) J.Y.Hwang, L.A.Arnold, F.Zhu, A.Kosinski, T.J.Mangano, V.Setola, B.L.Roth, R.K.Guy, J. .Med.Chem.2009,52,3892-3901; c) K.Biswas, T.A.N.Peterkin, M.C.Bryan, L.Arik, S.G.Lehto, H.Sun, F....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/784C07C49/813C07C49/84C07C49/782C07C49/792C07C49/76C07C49/563C07D307/46C07C45/26
Inventor 马娟渠攀攀李峰
Owner NANJING UNIV OF SCI & TECH
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