Synthesis method of 2-tetralone derivative

A technology of tetralone and a synthetic method, which is applied in the chemical field, can solve problems such as high cost, expensive raw materials, and environmental pollution, and achieve the effects of high yield, low cost, and mild reaction conditions

Inactive Publication Date: 2013-08-07
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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Problems solved by technology

The synthesis methods of 2-tetralone derivatives reported in many literatures can be divided into two categories: (1) one kind takes benzene and gamma-butyrolactone as raw materials and takes place Friedel-Crafts acylation reaction under the action of acidic catalyst Synthetic, but this method raw material is expensive, and cost is high, produces a large amount of waste gas waste residues, causes serious environmental pollution; (2) another kind is to use CrO 3 Oxidation of tetralin to synthesize 2-tetralone, but need to add CrO in the oxidation process 3 , will also cause serious environmental pollution

Method used

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  • Synthesis method of 2-tetralone derivative
  • Synthesis method of 2-tetralone derivative
  • Synthesis method of 2-tetralone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The reaction formula of the present embodiment is:

[0028]

[0029] In a reaction tube sealed at one end, add 364 mg of (E)-1-(2-iodophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (MW=364, 1.0 mmol), 480mg diethyl malonate (MW=160, 3mmol), then add 160mg NaOH (MW=40, 4mmol), 26mg L-hydroxyproline (MW=130, 0.2mmol), 19mg CuI (MW =190, 0.1mmol), 2.0mlDMSO as a solvent, under the protection of argon, the time of the series reaction is to stir and react at 20°C for 24h, dilute the reaction mixture with 10ml of water, extract twice with 2×10ml of ethyl acetate, The organic phases were combined, dried and spin-dried under reduced pressure to obtain a crude product. Column chromatography of petroleum ether: ethyl acetate = 10:1 gave 398 mg of the product, 1-tetralone derivative, with a yield of 98%.

[0030] The spectrum of the product: 1H NMR (CDCl3, 400MHz) δ8.13 (d, J=8.0Hz, 1H), 7.72 (d, J=8.0Hz, 1H), 7.63 (t, J=7.6Hz, 1H), 7.49(t, J=7.6Hz, 1H), 7.01(d, J=7.6Hz, 2H), 4.2...

Embodiment 2

[0032]

[0033] In a reaction tube sealed at one end, add 334mg (E)-1-(2-iodophenyl)-3-phenylprop-2-en-1-one (MW=364, 1.0mmol), 226mg cyanoacetic acid Ethyl ester (MW=113, 2mmol); then add 652mg Cs2CO3 (MW=325, 2mmol), 36mg 2-pyridinecarboxylic acid (MW=123, 0.3mmol), 14mg CuBr (MW=141, 0.1mmol), 3.0ml DMSO As a solvent, under the protection of nitrogen, the time for the series reaction was to stir the reaction at 30° C. for 18 hours; the other steps were the same as in Example 1, and finally 310 mg of the product 1-tetralone derivative was obtained, with a yield of 95%.

[0034] Product spectrum: 1H NMR (CDCl3, 400MHz) δ8.15 (d, J=8.0Hz, 1H), 7.74 (d, J=8.0Hz, 1H), 7.64 (t, J=8.4Hz, 1H), 7.51 (t, J=7.6Hz, 1H), 7.19-7.16(m, 3H), 7.09-7.06(m, 2H), 4.32(t, J=5.6Hz, 1H), 4.23-4.10(m, 2H), 3.56(dd, J=5.6Hz, J=17.2Hz, 1H), 3.19(dd, J=6.4Hz, J=17.2Hz, 1H), 1.20(t, J=7.2Hz, 3H), 13C NMR (CDCl3 , 75MHz) δ196.0, 169.6, 168.5, 139.8, 137.8, 133.3, 132.6, 131.9, 128.8, 128.5, 128.3,...

Embodiment 3

[0036]

[0037] In a reaction tube sealed at one end, add 364mg (E)-1-(2-iodophenyl)-3-(3-methoxyphenyl)prop-2-en-1-one (MW=364, 1.0 mmol), 195mg ethyl acetoacetate (MW=130, 1.5mmol), then add 120mg NaOH (MW=40, 3mmol), 52mgL-hydroxyproline (MW=130, 0.4mmol), 19mg CuI (MW=190 , 0.1mmol), 4.0ml DMSO as a solvent, under the protection of nitrogen, the time of the series reaction is to stir the reaction at 35°C for 18h, dilute the reaction mixture with 10ml of water, extract twice with 2×10ml of ethyl acetate, combine the organic phase, dried and spin-dried under reduced pressure to obtain a crude product, petroleum ether: ethyl acetate = 10:1 column chromatography to obtain 360 mg of the product, namely 1-tetralone derivative, with a yield of 98%.

[0038]The spectrum of the product: 1H NMR (CDCl3, 400MHz) δ8.14 (d, J=7.6Hz, 1H), 7.74 (d, J=8.0Hz, 1H), 7.63 (t, J=7.2Hz, 1H), 7.49(t, J=7.6Hz, 1H), 7.08(t, J=8.0Hz, 1H), 6.72(d, J=6.4Hz, 1H), 6.65-6.62(m, 2H), 4.29(t, J =6.0Hz...

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Abstract

The invention discloses a synthesis method of 1-tetralone derivative, which comprises the step of: in the environment of organic solvent and alkali, leading a compound with a structure of formula 1 and a compound with a structure of formula 2 to have cascade reaction under the action of ligand and catalyst. The synthesis method has raw materials with lower price, is low in cost and mild in reaction condition, causes no environmental pollution, and has the highest yield of 98%.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a method for synthesizing 1-tetralone derivatives. Background technique [0002] 1-tetralone derivatives are a class of important fine organic intermediates, widely used in liquid crystal and pharmaceutical industries, such as 4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene is an anti- The key intermediate of the depressant sertraline hydrochloride, 6-methoxytetralone is an important intermediate for the synthesis of family planning drugs. The synthesis methods of 2-tetralone derivatives reported in many literatures can be divided into two categories: (1) one kind is to take benzene and gamma-butyrolactone as raw materials to undergo Friedel-Crafts acylation reaction under the action of acid catalyst Synthetic, but this method raw material is expensive, and cost is high, produces a large amount of waste gas waste residues, causes serious environmental pollution; (2) another kind is to use...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/757C07C67/347C07C69/76C07C255/47C07C253/30C07C255/56C07C205/55C07C205/56C07C201/12C07D213/61C07D333/22C07D307/46
Inventor 哈成勇李正球蔡倩沈敏敏
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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