Whitby group

3-Heptyn-1-ol (10.0 g, 89.3 mmol) was added to p-toluene sulphonyl chloride (16.9 g, 89.0 mmol) in anhydrous pyridine (39.5 g, 500 mmol) at 0-5 °C.  After stirring overnight at room temperature, the reaction mixture was cooled to 0 ^°C and 6M HCL (30.0 mL) was added.  The product was extracted into diethyl ether (3 x 100 mL) and the combined organic extracts washed with water (4 x 100 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 product as a yellow oil (17.32 g, 65 mmol, 73 %).