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Method for producing aromatic unsaturated compound

A compound, unsaturated technology, applied in the field of preparation of aromatic unsaturated compounds

Inactive Publication Date: 2008-07-23
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is limited to compounds in which the nitrogen atom constituting the indole ring is protected by a benzenesulfonyl group, and in order to obtain the target product in good yield, it is required to use an excessive amount of expensive re-oxidant such as silver acetate.

Method used

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  • Method for producing aromatic unsaturated compound
  • Method for producing aromatic unsaturated compound
  • Method for producing aromatic unsaturated compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] 1.01g 3-(4-fluorophenyl)-1-isopropyl-1H-indole, 0.92g 3,3-dimethoxymethyl propionate, 0.72ml 90% by weight of aqueous acetic acid (containing 4mmol water) and 6 ml of glacial acetic acid were mixed, and then 0.33 g of phosphorus oxychloride was added dropwise to the mixture at an internal temperature of 25° C., and stirred at the same temperature for 9 hours to make it react. After the reaction, 16 ml of water was added dropwise to the reaction liquid, and the precipitated crystals were collected by filtration. The crystals were washed with 20% by volume of aqueous methanol, and then dried to obtain 1.25 g of trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl ] methyl acrylate (yellow solid). The yield is 93%.

[0078] 1 H-NMR (δ / ppm, CDCl 3 , 400MHz)

[0079] 1.70(6H, d, J=7Hz), 3.76(3H, s), 4.95(1H, m), 5.96(1H, d, J=16Hz), 7.50(1H, d, J=8Hz), 7.57(1H , d, J=8Hz), 7.08-7.40 (6H, m), 7.82 (1H, d, J=16Hz)

Embodiment 2

[0081] Mix 1.04g of 1-methyl-2-phenyl-1H-indole, 0.64g of trans-3-methoxymethyl acrylate, 94.5mg of water and 6ml of glacial acetic acid. To the mixture was added 124 mg of phosphorus oxychloride and stirred at the same temperature for 17 hours to allow a reaction. After the reaction, 30 ml of water was added dropwise to the reaction liquid, and then 50 ml of ethyl acetate was added for extraction, and the obtained organic layer was concentrated. The obtained concentrated residue was purified by flash chromatography to obtain 1.11 g of methyl trans-3-(1-methyl-2-phenyl-1H-indol-3-yl)acrylate (yellow solid). The yield was 76%.

[0082] 1 H-NMR (δ / ppm, CDCl 3 , 400MHz)

[0083] 3.64(3H, s), 3.74(3H, s), 6.46(1H, d, J=16Hz), 7.29-7.55(9H, m), 7.72(1H, d, J=16Hz)

Embodiment 3

[0085] 1.68 g of 1,3,5-trimethoxybenzene, 2.32 g of trans-methyl 3-methoxyacrylate, 0.18 g of water and 6 ml of glacial acetic acid were mixed, and at an internal temperature of 25° C., 164 mg of Phosphorus oxychloride was stirred at the same temperature for 3 hours to make it react. After the reaction was completed, 36 ml of water was added dropwise to the reaction solution, and the precipitated crystals were collected by filtration. The crystals were washed with 20% by volume of aqueous methanol and then dried to obtain 2.28 g of trans-methyl 3-(2,4,6-trimethoxyphenyl)acrylate (white solid). The yield was 91%.

[0086] 1 H-NMR (δ / ppm, CDCl 3 , 400MHz)

[0087] 3.79(3H, s), 3.85(3H, s), 3.87(6H, s), 6.12(2H, s), 6.76(1H, d, J=16Hz), 8.08(1H, d, J=16Hz)

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PUM

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Abstract

A method for producing an aromatic unsaturated compound represented by the formula (4): (wherein Ar represents an aromatic group which may be substituted or a heteroaromatic group which may be substituted, and Y represents an electron-withdrawing group) is disclosed which includes a step for reacting (a) a compound represented by the formula (1): (wherein Ar is as defined above), with (b) a compound represented by the formula (2): (wherein Y is as defined above, and Z represents a lower alkoxy), or a compound represented by the formula (3): (wherein Y and Z are as defined above), in the presence of (c) an acid or a compound which produces a mineral acid through hydrolysis.

Description

technical field [0001] The present invention relates to a method for the preparation of aromatic unsaturated compounds. Background technique [0002] The aromatic unsaturated compound represented by the formula (4) (hereinafter referred to simply as the aromatic unsaturated compound (4)) can be used, for example, as a synthetic intermediate of pharmaceuticals and agricultural chemicals. [0003] [0004] (In the formula, Ar represents an optionally substituted aromatic group or an optionally substituted heteroaromatic group, and Y represents an electron-withdrawing group.) [0005] For example known compound shown in following formula (7): [0006] [0007] It is a synthetic intermediate of fluvastatin, which is effective as a drug for hyperlipidemia, as described in, for example, WO01 / 92223. [0008] The compounds represented by the following formulas (8) and (9) are compounds being developed as therapeutic agents for arteriosclerosis as described in JP-A-9-202775 a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/04C07C67/343C07C69/734C07D209/10
Inventor 王维奇池本哲哉
Owner SUMITOMO CHEM CO LTD
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