Ethyl Acetate → 3-Methoxy-3-methylbutyl 2-(trifluoromethyl)benzenesulfonate

Participants

Reaction Steps

To a solution of 3-methoxy-3-methylbutane-1-ol (2.8 g, 24 mmol) and TEA (1.6 g, 16 mmol) in CH2Cl2 (15 mL) was added o-(trifluoromethyl)benzenesulfonyl chloride (1.9 g, 8 mmol) dissolved in CH2Cl2 (20 mL). The solution was stirred at rt for 4 h. Saturated aqueous NaHCO3 (15 mL) was added to the solution and mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (75 mL) and washed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography with ethyl acetate in hexanes yielded the desired product (2.1 g, 81%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.91 (m, 1H), 7.74 (m, 2H), 4.25 (t, 2H, J=7.5 Hz), 3.10 (s, 1H), 1.92 (t, 2H, J=7.5 Hz) 1.13 (s, 6H). Anal. Calcd. For C13H17F3O4S: C, 47.85; H, 5.25. Found: C, 47.95; H, 5.11.

Provenance & Evidence