Water → Toluene-4-sulfonic acid tetrahydro-furan-3-ylmethyl ester

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Reaction Steps

To a solution of tetrahydro-3-furanmethanol (Aldrich, 1.0 mL, 10.4 mmol) in 5 mL CH2Cl2 and 5 mL pyridine was added para-toluenesulfonyl chloride (3.0 g, 15.6 mmol) portion-wise over 15 minutes. This mixture stirred at ambient temperature for 3 hours then 5 mL H2O was added. The layers were separated and the aqueous layer was extracted 2×5 mL CH2Cl2. The combined organics were dried over Na2SO4, filtered, concentrated under reduced pressure and dried under vacuum (˜1 mm Hg) to afford the title compound (2.62 g, 10.2 mmol, 98% yield). 1H NMR (300 Mhz, CDCl3) δ ppm 1.49-1.63 (m, 1H) 1.94-2.08 (m, 1H) 2.46 (s, 3H) 2.52-2.68 (m, 1H) 3.49 (dd, J=9.16, 5.09 Hz, 1H) 3.64-3.84 (m, 3H) 3.88-4.03 (m, 2H) 7.36 (d, J=8.14 Hz, 2H) 7.76-7.82 (m, 2H); MS (DCI/NH3) m/z 257 (M+H)+.

Provenance & Evidence