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Synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde

A technology of diphenylbutanal and a synthesis method, which is applied in the synthesis of 2-methyl-4-carbonyl-2,4-diphenylbutanal and the synthesis field of 1,4-ketoaldehyde compounds, can solve the problem of strict Harsh reaction conditions, expensive catalysts, difficulties, etc., to achieve the effect of a wide range of substrates, good tolerance, and mild reaction conditions

Active Publication Date: 2017-12-29
NANJING UNIV OF TECH
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Problems solved by technology

However, these methods have disadvantages, such as the need for expensive catalysts; harsh reaction conditions; difficulties in preparing different carbonyl functional groups carrying α-quaternary stereocenters, etc.

Method used

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  • Synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde
  • Synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde
  • Synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde

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Embodiment 1

[0025] To a solution of acetophenone (5.0 mmol, 1.0 equiv) in toluene (5.0 mL) was added 1,1-dimethoxy-N,N-dimethylmethylamine (7.0 mmol, 1.4 eq.), stirred And be warmed up to 110 ℃, after the completion of the reaction (monitored by TLC), quenched with water, extracted with ethyl acetate, dried with anhydrous sodium sulfate, then the dried reaction mixture was concentrated under reduced pressure, and passed through column chromatography (hexane Alkane: ethyl acetate = 1:1) to obtain (E)-3-(dimethylamino)-1-phenylprop-2-en-1-one.

[0026] A solution of p-toluenesulfonylhydrazide (5 mmol) in methanol (5 mL) was stirred at 60 °C until p-toluenesulfonylhydrazide was completely dissolved, then acetophenone was slowly added dropwise to the mixture, and a solid precipitate was obtained after standing , the solid precipitate was washed with petroleum ether to obtain p-toluenesulfonyl hydrazone, which was stored in vacuum for later use;

[0027] Using a one-pot method, mix (E)-3-(dim...

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Abstract

The invention relates to a synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde. The synthetic method comprises the following steps: firstly adding 1,1-dimethoxy-N,N-dimethyl methylamine into a methylbenzene solution of acetophenone, after stirring and performing a heating reaction, quenching a product with water, and then carrying out extraction, drying and purification to obtain (E)-3-(dimethyl amino)-1-phenylprop-2-ene-1-ketone; slowly dropwise adding acetophenone into a methanol solution of p-toluenesulfonhydrazide to obtain p-toluenesulfonylhydrazone; and carrying out a reaction on (E)-3-(dimethyl amino)-1-phenylprop-2-ene-1-ketone, p-toluenesulfonylhydrazone, copper hydroxide and potassium carbonate in argon shield, and purifying a reaction product to obtain 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde. The method is wide in substrate application range, the tolerance for various functional groups is high, cheap copper is taken as a catalyst, and the reaction condition is mild; and a synthetic 1,4-ketoaldehyde compound can be easily converted into various useful synthetic structures, and carries an alpha-quaternary three-dimensional center.

Description

technical field [0001] The invention relates to a method for synthesizing 1,4-ketoaldehyde compounds, in particular to a method for synthesizing 2-methyl-4-carbonyl-2,4-diphenylbutyraldehyde, which belongs to the technical field of organic synthesis. Background technique [0002] 1,4-ketoaldehydes are widely used in many pharmaceuticals and are common skeletons in bioactive molecules. Typical 1,4-ketoaldehyde compounds are: [0003] [0004] The more common one is 2-methyl-4-carbonyl-2,4-diphenylbutyraldehyde. [0005] In the prior art, the synthesis methods of 1,4-ketoaldehydes mainly include: oxidation of hydroxyaldehydes or hydroxyketones or 1,4-diols; dearomatization of furan derivatives; ozonolysis of γ-ketoalkenes ; Intramolecular isomerization; Intermolecular coupling of two different carbonyl groups. Other methods include noble metals as catalysts for acylation reactions; small ring openings and Tsuji-Wacker oxidation reactions. However, these methods have dis...

Claims

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Application Information

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IPC IPC(8): C07C49/86C07C45/00C07C221/00C07C225/14C07C303/40C07C311/49
CPCC07C45/00C07C221/00C07C303/40C07B2200/07C07C225/14C07C311/49C07C49/86
Inventor 姜耀甲倪美燕张建国梁晓禹罗德平
Owner NANJING UNIV OF TECH
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