Pyridine → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

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A solution of toluene sulfonyl chloride (Aldrich, 38 g) and triethylene glycol monomethyl ether (Aldrich, 16.4 g) in dry pyridine (150 ml) was stirred at 0° C. (icebath) for 4 h, followed by 18 h at ambient temperature. The solution was then poured onto ice water (500 ml) and extracted with diethyl ether (3×300 ml). The ether extracts were combined, washed with hydrochloric acid (3 N) and water, dried (sodium sulfate), and concentrated to provide triethylene glycol methyl tosyl ether as a colorless oil (20.0 g, 62% based on glycol), 1H-NMR (CDCl3) δ: 7.75 (d, J=8.0 Hz, 2, 2 phenyl CH), 7.30 (d, J=8.1 Hz, 2, 2 phenyl CH), 4.11 (t, J=4.8 Hz, 2, CH2OS), 3.65-3.41 (m, 10, 5 CH2O), 3.32 (s, 3, CH3O ) and 2.40 (s, 3, benzylic CH3).

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