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1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone and preparation method thereof

A technology based on ethyl formate and ferrocene, which is applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve the problems of large solvent usage, low yield, long reaction time, etc. Short, simple reaction process, low equipment requirements

Inactive Publication Date: 2015-03-25
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the preparation of existing ketone compounds is mostly based on the liquid phase reflux method, which has the disadvantages of long reaction time, low yield, and large solvent usage.

Method used

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  • 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Weigh 0.0012mol ethyl acetoacetate, 0.0012mol anhydrous K 2 CO 3 Put it in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-phenyl-propenone, mix and grind. The mixture will become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-phenyl-3-(1-acetyl-1-carboxyethyl-methine)-propanone. Yield 80%, m.p. 125°C-126°C.

[0058] IR (KBr tablet, v / cm -1 ):2985, 1719, 1647, 1594, 1451, 1374, 1238;

[0059] 1 H-NMR: 7.20-7.71 (m, 5H, Ar-H), 4.97 (s, 2H, C 5 h 4 ), 4.65(s, 2H, C 5 h 4 ), 4.28(s, 5H, C 5 h 5 ), 4.01 (q, 2H, -OCH 2 ), 1.69 (s, 3H, COCH 3 ), 1.30(t, 3H, CH 2 CH 3 );

[0060] 13 C-NMR: 192.3, 158.2, 140.4, 135.0, 129.5, 128.5, 122.5, 43.6, 22.8, 13.8.

Embodiment 2

[0062] Weigh 0.0012mol ethyl acetoacetate, 0.0012mol anhydrous K 2 CO 3 Place in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-(p-chlorophenyl)-propenone, mix and grind. The mixture will become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-(p-chlorophenyl)-3-(1-acetyl-1-carboxyethyl-methine)-propanone. The yield was 77%, M.p. 143°C-144°C.

[0063] IR (KBr tablet, v / cm -1 ):2993, 1721, 1649, 1591, 1494, 1453, 1378, 1238;

[0064] 1 H-NMR: 7.16-7.63 (m, 4H, Ar-H), 4.96 (s, 2H, C 5 h 4 ), 4.66(s, 2H, C 5 h 4 ), 4.27(s, 5H, C 5 h 5 ), 4.02 (q, 2H, -OCH 2 ), 2.35(s, 3H, COCH 3 ), 1.33(t, 3H, CH 2 CH 3 );

[0065] 13 C-NMR: 192.1, 159.8, 138.9, 135.6, 133.7, 128.9, 122.9, 43.1, 23.1, 13.9.

Embodiment 3

[0067] Weigh 0.0012 mol of ethyl acetoacetate, 0.0012 mol of NaOH were placed in a mortar and quickly mixed evenly, then 0.001 mol of 1-ferrocenyl-3-(p-bromophenyl)-propenone was added, mixed and ground. The mixture will become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-(p-bromophenyl)-3-(1-acetyl-1-carboxyethyl-methine)-propanone. Yield 73%, m.p. 162°C-163°C.

[0068] IR (KBr tablet, v / cm -1 ):2987, 1712, 1649, 1592, 1485, 1453, 1375, 1238;

[0069] 1 H-NMR: 7.12-7.77 (m, 4H, Ar-H), 4.94 (s, 2H, C 5 h 4 ), 4.64(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 4.02 (q, 2H, -OCH 2 ), 2.23 (s, 3H, COCH 3 ), 1.14(t, 3H, CH 2 CH 3 );

[0070] 13 C-NMR: 191.2, 143.1, 138.9, 129.5, 122.0, 121.9, 119.5, 58.7, 43.0, 27.0, 13.6.

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Abstract

The invention discloses 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone and a preparation method thereof. The general structural formula of the 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone is shown in the specification, wherein the aryl group is phenyl group, halogenbenzyl group, methyl phenyl group, ethyl phenyl group, propyl phenyl group, methoxy phenyl group, nitrophenyl group, hydroxyphenyl group, aminophenyl group, styryl group, five-membered heterocyclic group or six-membered heterocyclic group. The preparation method of the 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone comprises the following steps: adding A mol of 1-ferrocenyl-3-aryl-acrylketone, B mol of anhydrous K2CO3 (or NaOH) and C mol of ethyl acetoacetate into a dry mortar to quickly grind; performing TLC (Thin Layer Chromatography) monitoring until the reaction is complete; then washing, performing extraction filtration and drying to obtain the 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formylcarbethoxyl-methenyl)-acetone. The method has the advantages of short reaction time, no need of solvent, environment friendliness, economy, easiness in operation, mild reaction condition, easiness in post-treatment and high yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-(1-acetyl-1-formyl ethyl-methine)-acetone and a preparation method thereof. Background technique [0002] Michael addition is the nucleophilic addition reaction of enolate (or similar) anion to the carbon-carbon double bond of a, β-unsaturated ketone, aldehyde, ester or carboxylic acid derivative, and is also an active methylene compound A method of alkylation reaction, which is a classic organic reaction. [0003] Grinding is one of the important means to promote solid-phase organic reactions. The reason why the grinding method can accelerate the reaction is that the external force activates the system by increasing the total free energy of the reaction system through frictional heat generation and the following two effects: (1) The surface free energy increases, which is because the solid (2) The stored elastic tension energy, which is because...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 尹大伟宋思梦刘玉婷尹静怡王金玉杨阿宁刘蓓蓓黄涛
Owner SHAANXI UNIV OF SCI & TECH
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