Preparation method of 7-methoxy-3-phenyl-1,2-dihydronaphthalene

A technology of methoxyphenylmethylenecyclopropane and methoxy, applied in the field of preparation of 7-methoxy-3-phenyl-1,2-dihydronaphthalene, can solve the problem of low yield of target product , long synthetic route, high synthetic cost and other problems, to achieve the effect of low cost, mild reaction conditions and high yield

Active Publication Date: 2019-07-02
HUNAN FIRST NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the defects of long synthetic route, low yield of target product, high synthetic cost and low efficiency in the

Method used

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  • Preparation method of 7-methoxy-3-phenyl-1,2-dihydronaphthalene

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Effect test

Embodiment 1

[0023] To a Slenk lock reactor, add 4-methoxyphenylmethylenecyclopropane (48mg, 0.3mmol), benzenesulfonyl chloride (3eq, 158mg), Ru(bpy) 3 Cl 2 ·6H 2 O (11.2mg, 5mol%), Na 2 CO 3 (2eq, 63.6mg) and acetonitrile (2mL), then the reactor was replaced with nitrogen for 3 times, and reacted for 12 hours at room temperature and 24W energy-saving lamp lighting conditions, and the reaction was completely detected by TLC or GC, and then the reaction solution was filtered through filter paper The catalyst mixture was recovered and dried, the filtrate was concentrated in vacuo, and the residue was separated by silica gel column chromatography (the elution solvent was n-hexane / ethyl acetate mixed solvent, the volume ratio was 50:1) to obtain 7-methoxy-3- 64 mg of phenyl-1,2-dihydronaphthalene, yield 90.4%.

Embodiment 2

[0025] To a Slenk lock reactor, add 4-methoxyphenylmethylenecyclopropane (48 mg, 0.3 mmol), benzenesulfonyl chloride (3 eq, 158 mg), Eosin Y (9.7 mg, 5 mol%), Na 2 CO 3 (2eq, 63.6mg) and acetonitrile (2mL), then the reactor was replaced with nitrogen for 3 times, and reacted for 24 hours at room temperature and under 24W energy-saving lighting conditions, and the reaction was detected by TLC or GC. Column filtration, vacuum concentration, and the residue was separated by silica gel column chromatography (eluting solvent was n-hexane / ethyl acetate mixed solvent, volume ratio was 50:1) to obtain 7-methoxy-3-phenyl-1 ,2-Dihydronaphthalene 51.7mg, yield 73%.

Embodiment 3

[0027] To a Slenk lock reactor, add 4-methoxyphenylmethylenecyclopropane (48mg, 0.3mmol), benzenesulfonyl chloride (3eq, 158mg), Ir(ppy)3 (9.8mg, 5mol%) , Na 2 CO 3 (2eq, 63.6mg) and acetonitrile (2mL), then the reactor was replaced with nitrogen for 3 times, and reacted at room temperature and 5W LED blue light for 12 hours, and the reaction was complete by TLC or GC detection, and then the reaction solution was passed through silica gel for a short time Column filtration, vacuum concentration, and the residue was separated by silica gel column chromatography (eluting solvent was n-hexane / ethyl acetate mixed solvent, volume ratio was 50:1) to obtain 7-methoxy-3-phenyl-1 ,2-Dihydronaphthalene 57.3mg, yield 81%.

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Abstract

The invention discloses a preparation method of 7-methoxy-3-phenyl-1,2-dihydronaphthalene. 4-methoxyphenylmethylene cyclopropane and benzenesulfonyl chloride are used as raw materials to directly prepare the 7-methoxy-3-phenyl-1,2-dihydronaphthalene. According to the method, the raw materials are easily available, compared with the prior art, the cost is remarkably reduced, and the process route is shortened. The technological condition of the method is a photo-oxidation reduction catalysis system, which has the advantages of mild reaction conditions, simplicity, feasibility, high target product yield, catalyst recycling and low cost.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 7-methoxy-3-phenyl-1,2-dihydronaphthalene. Background technique [0002] 7-Methoxy-3-phenyl-1,2-dihydronaphthalene is an important organic compound and is used as an intermediate for the preparation of nafaxidine / lasofoxifene (Chem.Eur.J.2018 , 24, 9066–9074). For example, Chinese patent CN103113323A, 20130522 reports the following synthesis process route for preparing lasofoxifene: [0003] However, the synthesis of the starting compound 1 in this synthetic route requires 6-methoxytetralone as a raw material to be prepared through a three-step reaction, and the reaction route is long; the preparation of intermediate 2 requires a SUZUKI coupling reaction , involving the use of expensive palladium catalytic systems. [0004] Barry M.Trost etc. have also reported a method for preparing 7-methoxy-3-phenyl-1,2-dihydronaphthalene, wh...

Claims

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Application Information

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IPC IPC(8): C07C41/30C07C43/21
CPCC07C41/30C07C2602/10C07C43/21Y02P20/584
Inventor 唐建生唐文萍
Owner HUNAN FIRST NORMAL UNIV
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