Potassium Hydroxide → 1-[2-(p-Ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

참여 물질

반응 단계

2-(p-Ethoxycarbonylphenoxy)-1-chloroethane is added in one portion to a mixture of 2-(1-imidazolyl)-3-methylindole (1.97 g), potassium hydroxide (0.62 g) and tetrabutylammonium bromide (0.32 g) in acetonitrile (250 ml) while stirring under nitrogen at room temperature. After stirring at room temperature for 65 hours an additional 0.64 g of tetrabutylammonium bromide is added and the mixture is refluxed for 41 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is concentrated in vacuo and the oil obtained dissolved in ethyl acetate and extracted with 1N hydrochlorid acid. The aqueous extract is made basic to pH 10 with 3N sodium hydroxide and extracted with ethyl acetate (3×100 ml). This extract is dried over magnesium sulfate, filtered, and concentrated in vacuo to give a crude oil which is purified by flash chromatography on silica gel. The product is eluted with 3% methanol in methylene chloride to give 1-[2-(p-ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole; NMR (CDCl3): δ 8.02 (d, 2H), 7.87-7.13 (m, 7H), 6.80 (d, 2H), 4.50-4.00 (m, 6H), 2.20 (s, 3H), 1.37 (t, 3H).

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