Potassium Hydroxide → 1-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole

Participants

Reaction Steps

To a mixture of 4.17 g of 3-methyl-2-(3-pyridyl)indole, 0.64 g of tetra-n-butyl ammonium bromide and 1.2 g of powdered KOH in 500 ml of acetonitrile, while stirring at room temperature under nitrogen, is added 5.06 g of ethyl p-(2-bromoethoxy)benzoate [for preparation see U.S. Pat. No. 2,790,825 (1957)]. The suspension is stirred for five days. After filtration to remove KBr, the filtrate is concentrated to an oil which is dissolved in ethyl acetate and extracted with 3 N HCl. The acid layer is separated and treated with 3 N NaOH. This suspension is extracted with ethyl acetate (3×100 ml) and the organic extract is separated, dried over MgSO4, and concentrated to give as an oil 1-[2-(4-ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole.

Provenance & Evidence