Iodoethane → 2-Ethyl-4-(5-methyl-2-furyl)-butane nitrile

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diethyl amide prepared from 0.7 g (0.1 mol) lithium and 7.3 g (0.1 mol) diethyl amine in 44 ml benzene/hexamethyl phosphoric acid triamide 1:1 (2 hours at 25° C.) was added dropwise under nitrogen to a mixture which had been cooled down to -70° C. of 14.9 g (0.1 mol) 4-(5-methyl-2-furyl)-butane nitrile, 15.6 g (0.1 mol) ethyl iodide, 20 ml dry tetrahydrofurane and 140 ml dry ether. The mixture obtained was stirred for one hour at -70° C., was slowly heated up to 10° C. and then poured into cold water. The organic layer was separated off, washed with water and dried on anhydrous magnesium sulphate. The solvent was evaporated off under reduced pressure and the residue was subjected to chromatography over 300 g silicagel with hexane/ethyl acetate 95:5. Initially 2.3 g dl-2,2-diethyl-4-(5-methyl-2-furyl)-butane nitrile was eluated, followed by 9.5 g (58% yield) dl-2-ethyl-4-(5-methyl-2-furyl)-butane nitrile.

Provenance & Evidence