Reaction #1973941

Reaction equation

NaHCO3

ethyl acetate

1,3-butane diol

o-(trifluoromethyl)benzenesulfonyl chloride

→

desired product

Yield 84.0%

3-Hydroxybutyl 2-(trifluoromethyl)benzenesulfonate

Yield 84.0%

Solvents

CH2Cl2

—

hexanes

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGwas stirred at rt for 45 min
2. 2
   ExtractionThe organics were extracted with CH2Cl2 (150 mL)
3. 3
   Washwashed with 0.5 M HCl (2×80 mL) and saturated aqueous NaCl (1×50 mL)
4. 4
   DryingThe organics were dried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   Otherto give a crude mixture

Procedure

To a solution of 1,3-butane diol (2.18 g, 24 mmol) and TEA (1.64 g, 16 mmol) in CH2Cl2 (15 mL) at 0° C. was added o-(trifluoromethyl)benzenesulfonyl chloride (2 g, 8 mmol) dissolved in CH2Cl2 (20 mL). The solution was stirred at 0° C. for 2 h. Saturated aqueous NaHCO3 (15 mL) was added to the solution and mixture was stirred at rt for 45 min. The organics were extracted with CH2Cl2 (150 mL) and washed with 0.5 M HCl (2×80 mL) and saturated aqueous NaCl (1×50 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography (50% ethyl acetate in hexanes) yielded the desired product (2 g, 84%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.92 (m, 1H), 7.74 (m, 2H), 4.34 (m, 1H), 4.24 (m, 1H), 3.95 (m, 1H), 1.89 (m, 1H), 1.73 (m, 1H), 1.20 (d, 3H, J=6.3 Hz). Anal. Calcd. For C11H13F3O4S: C, 44.29; H, 4.39. Found: C, 44.29; H, 4.28.

Source