3-Methoxy-1-butanol → 3-Methoxybutyl 4-(trifluoromethyl)benzenesulfonate

Participants

Reaction Steps

To a solution of 3-methoxybutane-1-ol (12) (0.58 g, 4.9 mmol) in pyridine (5 mL) was added p-(trifluoromethyl)-benzenesulfonyl chloride (0.98 g, 4 mmol). The solution was stirred at rt for 3.5 h. The reaction mixture was diluted with ethyl acetate (25 mL) and washed with 1 M HCl (6×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL). The organics were dried over Na2SO4 and concentrated to give an oil (13) (0.53 g, 40%). 1H NMR (400 MHz CDCl3) δ 8.03 (d, 2H, J=8.1 Hz), 7.81 (d, 2H, J=8.3 Hz), 4.19 (m, 2H), 3.35 (m, 1H), 3.18 (s, 3H), 1.78 (m, 2H), 1.09 (d, 3H, J=6.0 Hz); 19F δ (s). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 45.99; H, 4.64.

Provenance & Evidence