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A method for decarboxylation and oxidative coupling of α, β-unsaturated carboxylic acid and cyclic ether compound

A technology for carboxylated couples and compounds, which is applied in the field of organic intermediate synthesis and achieves the effects of high yield, mild reaction conditions and short process flow

Active Publication Date: 2018-07-31
常州田上环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Aiming at the defect that a transition metal catalyst must be used in the cross-oxidative coupling reaction of the existing α, β-unsaturated carboxylic acid and the decarboxylation oxidation of the cyclic ether compound, the purpose of the present invention is to provide a non-transition metal catalyzed, Method for realizing cross-oxidative coupling reaction of decarboxylation of α,β-unsaturated carboxylic acid and cyclic ether compound with high selectivity and high yield under mild reaction conditions

Method used

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  • A method for decarboxylation and oxidative coupling of α, β-unsaturated carboxylic acid and cyclic ether compound
  • A method for decarboxylation and oxidative coupling of α, β-unsaturated carboxylic acid and cyclic ether compound
  • A method for decarboxylation and oxidative coupling of α, β-unsaturated carboxylic acid and cyclic ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] α, β unsaturated carboxylic acid:

[0073] Ketone compounds:

[0074] Yellow oil, yield 88%;

[0075] 1 H NMR(400MHz, CDCl 3 )δ:7.97(d,J=7.7Hz,2H), 7.56(t,J=7.3Hz,1H), 7.46(t,J=7.5Hz,2H), 4.44–4.38(m,1H), 3.91– 3.87(dd,J=14.6,7.2Hz,1H), 3.76–3.75(dd,J=14.8,7.4Hz,1H), 3.43–3.37(dd,J=16.3,6.1Hz,1H), 3.09–3.03( dd, J = 16.3, 6.7 Hz, 1H), 2.23–2.16 (dt, J = 13.0, 6.5 Hz, 1H), 1.98–1.88 (m, 2H), 1.61–1.52 (m, 1H).

[0076] 13 C NMR(100MHz, CDCl 3 )δ: 25.6, 31.6, 44.6, 67.8, 75.4, 128.2, 128.6, 133.1, 137.0, 198.4.

Embodiment 2

[0078] α, β unsaturated carboxylic acid:

[0079] Ketone compounds:

[0080] Yellow oily product with a yield rate of 90%;

[0081] 1 H NMR(400MHz, CDCl 3 )δ: 8.01–7.98(dd,J=8.5,5.5Hz,2H), 7.13(t,J=8.5Hz,2H), 4.44–4.35(m,1H), 3.90–3.86(dd,J=14.8, 7.0Hz,1H), 3.76–3.74(dd,J=14.8,7.4Hz,1H), 3.37–3.33(dd,J=16.1,6.3Hz,1H),3.05–3.00(dd,J=16.1,6.4Hz ,1H), 2.22–2.16(td,J=12.8,6.5Hz,1H),1.98–1.89(m,2H),1.62–1.53(ddd,J=16.1,12.5,7.9Hz,1H).

[0082] 13 C NMR(100MHz, CDCl 3 )δ: 25.5, 31.6, 44.5, 67.8, 75.3, 115.7, 130.8 (d, J C-F =9.3Hz),133.5(d,J C-F =3.0Hz),165.7(d,1J C-F =254.0Hz), 196.8.

Embodiment 3

[0084] α, β unsaturated carboxylic acid:

[0085] Ketone compounds:

[0086] Yellow oily product, yield 92%;

[0087] 1 H NMR(400MHz, CDCl 3 )δ:7.90(d,J=8.2Hz,2H),7.43(d,J=8.2Hz,2H),4.42–4.35(m,1H),3.90–3.88(dd,J=14.6,7.3Hz,1H ), 3.78–3.74(dd,J=14.9,7.4Hz,1H), 3.37–3.31(dd,J=16.2,6.3Hz,1H),3.03–2.99(dd,J=16.2,6.3Hz,1H), 2.22–2.15(td,J=12.8,6.5Hz,1H),1.98–1.88(m,2H),1.61–1.52(dq,J=12.5,8.0Hz,1H).

[0088] 13 C NMR(100MHz, CDCl 3 )δ: 25.5 31.5, 44.5, 67.8, 75.3, 128.8, 129.6, 135.3, 139.5, 197.2

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Abstract

The invention discloses a method of decarboxylation oxidative coupling for [alpha], [beta]-unsaturated carboxylic acid and a cyclic ether compound. In the method, under an oxygen-containing atmosphere, the [alpha], [beta]-unsaturated carboxylic acid and the cyclic ether compound are subjected to a one-pot reaction in the presence of persulfate to generate a ketone compound. The method is carried out under catalysis of non-transition metal and mild reaction conditions, has high selectivity and yield, is simple in operations and low in cost, and is beneficial to industrial production.

Description

Technical field [0001] The invention relates to a decarboxylation oxidative coupling reaction of α, β-unsaturated carboxylic acid and cyclic ether compound, in particular to a decarboxylation oxidative coupling of α, β-unsaturated carboxylic acid and cyclic ether compound under non-metal catalysis conditions The method for preparing ketone compounds belongs to the field of organic intermediate synthesis. Background technique [0002] The transition metal-catalyzed decarboxylation coupling reaction has changed the pattern of new organic synthesis methods to a certain extent, and provided a new way to synthesize useful compounds, and at the same time improved the ability to synthesize important complex macromolecular compounds, so in the field of drug synthesis Has a unique application prospect. However, the classic decarboxylation coupling reaction must release an equimolar amount of carbon dioxide through the metal carboxylate, and form the corresponding organometallic intermedi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/12C07D405/06C07D409/06C07D307/46C07D333/22C07D207/08C07D317/26C07D317/46C07D309/06C07D319/12C07B41/06
CPCC07B41/06C07D207/08C07D307/12C07D307/46C07D309/06C07D317/26C07D317/46C07D319/12C07D333/22C07D405/06C07D409/06
Inventor 郭灿城吉朋意郭欣
Owner 常州田上环保科技有限公司