Pyridine,
p-toluene sulphonyl chloride,
dichloromethane (distilled from CaH₂),
but-3-yn-1-ol

But-3-yn-1-ol (1mL, 13.2mmol) is stirred in DCM (12mL) at 0^oC and p-toluene sulphonyl chloride (3.8g, 20mmol)) is added, followed by pyridine (2.2mL, 28.4mmol). The reaction is stirred at 0^oC until completion (TLC, about 3 hours) then diluted with ether (35mL) and washed consecutively with water, 1M HCl, NaHCO₃ (sat. soln.) and brine, dried over magnesium sulphate, filtered and concentrated. Purification is by column chromatography eluting with 15%EtOAc/PE, and yields are quantitative.

This is a more general procedure for tosylation than Page 80. It is very simple to carry out, and does not require the vast amount of pyridine used in that procedure as purification is by chromatography rather than crystallisation.

¹HNMR (CDCl₃, 300MHz) 7.85 (2H,d), 7.39 (2H, d), 4.16 (2H, t), 2.59(2H, dt), 2.44 (3H, s), 1.95 (1H, t)

G.Eglington, M.C.Whiting J.Chem.Soc. 1950 p.3650 doi:10.1039/jr9500003650

P. Garner and J. M. Park, J. Org. Chem. 1987, 52, 2361 doi:10.1021/jo00388a004
A. McKillop, R. J. K. Taylor, R. J. Watson and N. lewis, Synthesis, 1994, 31 doi:10.1055/s-1994-25398
A. Dondoni and D. Perrone, Synthesis 1997, 527 doi:10.1055/s-1997-1229