Whitby group

To a stirred solution of N-benzylallylamine (1.46g, 10.0 mmol), K₂CO₃ (2.0 g, 20.0 mmol) in MeCN (30.0 mL) at 0 °C, cinnamyl bromide (1.97 g, 10.0 mmol) was added dropwise.  The solution was warmed to room temperature, stirred for 1 hour then refluxed for 1 hour, quenched with a saturated solution of NaHCO₃ (50.0 mL).  The product was extracted into diethyl ether (3 x 40 mL), the combined organic layer washed with water (3 x 30 mL), brine (50.0 mL), dried over MgSO₄, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO₂, 0-100 % Et₂O:petroleum including 5 % Et₃N) afforded the title compound as an orange oil (2.31 g, 8.7 mmol, 87 %).