Method for synthesizing 1-cyclopropyl-naphthyl by virtue of 1-vinyl-naphthyl

A technology of cyclopropyl naphthalene and vinyl naphthalene, which is applied in the direction of condensation between hydrocarbons and non-hydrocarbons to produce hydrocarbons, organic chemistry, etc., can solve the problem of high cost, and achieve the effects of simple operation, mild reaction conditions and lower synthesis costs.

Inactive Publication Date: 2014-03-26
CHANGZHOU UNIV
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Problems solved by technology

[0005] In order to overcome the shortcoming of traditional synthetic 1-cyclopropylnaphthalene, the technical problem to be solved in the present invention is: in the synthetic technique of existing 1-cyclopropylnaphthalene, the raw mat...

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  • Method for synthesizing 1-cyclopropyl-naphthyl by virtue of 1-vinyl-naphthyl

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Experimental program
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Effect test

Embodiment 1

[0012] Under nitrogen protection and ice bath conditions, 154 g (1 mol) of 1-naphthylethylene was slowly added dropwise to 100 ml of 3 M Grignard reagent tert-butylmagnesium chloride. After the dropwise addition, 187 g (1 mol) of 1,2-dibromomethane and 667 ml of 3 M Grignard reagent tert-butylmagnesium chloride were added. After reacting for 6 hours, the reaction was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, and the ethyl acetate was distilled off under reduced pressure. Toluene was recrystallized to obtain 142 g of the product with a yield of 83%. Purity 99.1% (HPLC).

Embodiment 2

[0014] Under nitrogen protection and ice bath conditions, 154 g (1 mol) of 1-naphthylethylene was slowly added dropwise to 300 ml of Grignard reagent tert-butylmagnesium chloride with a concentration of 3 M. After the dropwise addition, 1043 g (6 mol) of 1,2-dibromomethane and 667 ml of 3 M Grignard reagent tert-butylmagnesium chloride were added. After reacting for 6 hours, the reaction was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, and the ethyl acetate was distilled off under reduced pressure. Toluene was recrystallized to obtain 142 g of the product with a yield of 83%. Purity 99.1% (HPLC).

[0015]

Embodiment 3

[0017] Under nitrogen protection and ice bath conditions, 154 g (1 mol) of 1-naphthylethylene was slowly added dropwise to 667 ml of 3 M Grignard reagent tert-butylmagnesium chloride. After the dropwise addition, 536 g (2 mol) of 1,2-diiodomethane and 450 ml of 3 M Grignard reagent tert-butylmagnesium chloride were added. After reacting for 3 hours, the reaction was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, and the ethyl acetate was distilled off under reduced pressure. Toluene was recrystallized to obtain 129 g of the product with a yield of 74%. Purity 99.3% (HPLC).

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Abstract

The invention discloses a method for synthesizing 1-cyclopropyl-naphthyl by virtue of 1-vinyl-naphthyl and belongs to the technical field of organic synthesis. The method comprises the steps of under nitrogen protection and the condition of and ice bath, slowly dripping 1-vinylnaphthalene into tert-butylmagnesium chloride as a Grignard reagent with the concentration of 3M, wherein the molar ratio of the 1-vinylnaphthalene to the tert-butylmagnesium chloride is 1:(0.3-2); after dripping, adding 1-6mol methylenehalide and 0.3-2mol tert-butylmagnesium chloride as the Grignard reagent with the concentration of 3M, after reacting for 1-6 hours, quenching the reaction by virtue of a saturated ammonium chloride solution, extracting by virtue of ethyl acetate, evaporating the ethyl acetate by virtue of decompression, and carrying out recrystallization by virtue of methylbenzene to obtain a product. With the adoption of the method, with the 1-vinylnaphthalene and the methylenehalide as cheap chemical products as initial raw materials, the 1-cyclopropyl-naphthyl is synthesized by virtue of a one-step method; as the reaction conditions are mild and the operation is convenient, the method is suitable for industrial large scale production, and the synthesis cost of the 1-cyclopropyl-naphthyl is greatly lowered.

Description

technical field [0001] The invention relates to a method for synthesizing 1-cyclopropylnaphthalene from 1-vinylnaphthalene, belonging to the technical field of organic synthesis. Background technique [0002] 1-Cyclopropylnaphthalene is an important intermediate in organic synthesis, widely used in organic and pharmaceutical synthesis. 1-cyclopropylnaphthalene medicine is mainly used in the synthesis of new allylamine antifungal drugs. Such drugs have less side effects and strong antifungal activity. Compared with traditional triazole antifungal drugs, they are antifungal drugs with more clinical prospects, and the market demand is gradually increasing. [0003] There are few domestic and foreign reports on its synthetic method, mainly the following two types: a) Use 1-bromonaphthalene as raw material, and condense with cyclopropylboronic acid. This method has a high yield and is widely used at present. However, the price of raw materials and catalysts is relatively high, ...

Claims

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Application Information

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IPC IPC(8): C07C13/47C07C2/88
Inventor 宋国强陆颖逊黄险峰张文楠
Owner CHANGZHOU UNIV
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