Triphenylphosphine (0.34 g, 0.0013 mol) was added in small portions to a solution of (E)-hex-2-en-1-ol (0.13 g, 0.0013 mol), 4-(4-pentylbicyclo[2.2.2]octyl)phenol (0.35 g, 0.0013 mol), diethylazodicarboxylate (0.22 g, 0.0013 mol) in dry tetrahydrofuran (20 cm3), cooled in an ice bath under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C./ethyl acetate mixture as eluent, followed by recrystallisation from ethanol to yield 0.18 g (39%), K 69° C., SA-N 59° C., N-I 134° C.
