Ethyl Acetate → 3-Hydroxy-3-methylbutyl 2,3,4,5,6-pentafluorobenzenesulfonate

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Reaction Conditions

Reaction Steps

To a solution of 3-methyl-1,3-butane diol (0.79 g, 7.5 mmol) and TEA (0.37 g, 3.6 mmol) in CH2Cl2 (7 mL) at) 0° C. was added pentafluorobenzenesulfonyl chloride (0.80 g, 3.0 mmol). The solution was stirred at 0° C. for 1.5 h. Saturated aqueous NaHCO3 (10 mL) was added to the solution and the mixture was stirred at rt for 15 min. The organics were extracted with CH2Cl2 and washed with 0.5 M HCl (1×20 mL) and saturated aqueous NaCl (1×20 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography with (30% ethyl acetate in hexanes) yielded the desired product as a white crystalline low melting point solid (0.69 g, 66%). 1H NMR (400 MHz CDCl3) δ 4.49 (t, 2H, J=7.0 Hz), 1.97 (t, 2H, J=7.0 Hz) 1.27 (s, 6H). Anal. Calcd. For C11H11F5O4S: C, 39.53; H, 3.32. Found: C, 39.54; H, 3.22.

Provenance & Evidence