N-Formylmorpholine → 5-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

1.48 g (4.47 mmol) of 2-[4-(4-propylcyclohexyl)phenyl]selenophene are initially introduced in 15 ml of diethyl ether, and 4.4 ml (7.0 mmol, 15% soln. in hexane) of n-BuLi are metered in rapidly. The mixture is heated under reflux for 15 min and subsequently cooled to −78° C. 1.4 ml (14.0 mmol) of N-formylmorpholine are added in one portion, and the mixture is warmed to RT and stirred for 24 h. The batch is diluted with MTBE, and 1 N hydrochloric acid is added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is recrystallised from n-heptane. 5-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde is obtained as a red solid.

Provenance & Evidence