Whitby group

To a solution of propane-1,3-diol (100 mmol, 7.61 g) and pyridine (95 mmol, 7.52 g) in chloroform (100 mL) at 0 °C was added para-toluene sulfonyl chloride (79 mmol, 15.06 g). The reaction was stirred for 3 h, when H₂0 (10 mL) and Et₂O (30 mL) were added. The layers were separated and the aqueous extracted with ether. The combined organic phases were washed with 2 M HCl (20 mL), NaHCO₃ solution (20 mL) and brine (20 mL), dried over MgSO₄, filtered and concentrated. The crude product was purified by column chromatography (SiO₂, 70% ether in petrol) providing the title compound as a viscous, colourless oil (9.524 g, 51%).