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Tosylation of an alcohol; toluene-4-sulphonic acid esters

SyntheticPage 155
DOI: 10.1039/SP155
Submitted Aug 30, 2001, published Aug 31, 2001
zac etheridge (zac.etheridge@orange.net)
A contribution from Caddick, Sussex


			Reaction Scheme: Tosylation of an alcohol

Chemicals Used

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

Procedure

But-3-yn-1-ol (1mL, 13.2mmol) is stirred in DCM (12mL) at 0oC and p-toluene sulphonyl chloride (3.8g, 20mmol)) is added, followed by pyridine (2.2mL, 28.4mmol). The reaction is stirred at 0oC 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.

Author's Comments

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.

Data

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)

Lead Reference

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

Other References

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

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Keywords: 155, alcohol, protection, toluene-4-sulphonic acid ester, tosyl, tosylation

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