Ammonia → 2-Methyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

3.4 g (10.3 mmol) of 2-[4-(4-propylcyclohexyl)phenyl]selenophene are initially introduced in 100 ml of diethyl ether, and 9.0 ml (14.3 mmol, 15% soln. in hexane) of n-BuLi are metered in rapidly. The mixture is heated under reflux for 25 min and subsequently cooled to −78° C. 1.60 ml (25.7 mmol) of methyl iodide are added in one portion, and the mixture is warmed to RT and stirred for 24 h. Sat. ammonium chloride soln. and conc. ammonia soln. are added, and the batch is stirred vigorously for a few minutes. The mixture is acidified using hydrochloric acid, and the organic phase is separated off. The aqueous phase is extracted with MTBE, and the combined organic phases are dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:EtOAc=25:1). The further purification is carried out by recrystallisation from ethanol and n-heptane. 2-Methyl-5-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as a colourless solid (m.p. 98° C.).

Herkunft & Nachweise