Reaction #1973943

Reaction equation

3-methoxybutane-1-ol

o-(trifluoromethyl)benzenesulfonyl chloride

ethyl acetate

→

desired product

Yield 54.4%

3-Methoxybutyl 2-(trifluoromethyl)benzenesulfonate

Yield 54.4%

Solvents

CH2Cl2

—

hexanes

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with 1 M HCl (3×15 mL), saturated aqueous NaHCO3 (1×15 mL) and saturated aqueous NaCl (1×15 mL)
2. 2
   DryingThe organics were dried over Na2SO4
3. 3
   Concentrationconcentrated
4. 4
   Otherto give a crude mixture

Procedure

To a solution of 3-methoxybutane-1-ol (0.63 g, 6.0 mmol) and TEA (0.42 g, 4.1 mmol), in CH2Cl2 (5 mL) was added o-(trifluoromethyl)benzenesulfonyl chloride (0.50 g, 2.0 mmol). The solution was stirred at rt for 2 h. The reaction mixture was diluted with CH2Cl2 (15 mL) and washed with 1 M HCl (3×15 mL), saturated aqueous NaHCO3 (1×15 mL) and saturated aqueous NaCl (1×15 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 (0.34 g, 50%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.91 (m, 1H), 7.75 (m, 2H), 4.24 (m, 2H), 3.40 (m, 1H), 3.21 (s, 3H), 1.80 (m, 2H), 1.10 (d, 3H, J=6.2 Hz). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 46.30; H, 4.88.

Source