Reaction #1973942

Reaction equation

NaHCO3

ethyl acetate

1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

Yield 40.6%

3-Hydroxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate

Yield 40.6%

Solvents

CH2Cl2

—

hexanes

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 30 min
2. 2
   ExtractionThe organics were extracted with CH2Cl2 (50 mL)
3. 3
   Washwashed with 0.5 M HCl (3×20 mL), saturated aqueous NaHCO3 (1×20 mL) and saturated aqueous NaCl (1×20 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 (0.9 g, 10 mmol) and TEA (0.61 g, 6 mmol) in CH2Cl2 (4 mL) at 0° C. was added pentafluorobenzenesulfonyl chloride (0.53 g, 2 mmol) dissolved in CH2Cl2 (4 mL). The solution was stirred for 6 h over which time the solution slowly warmed to rt. Saturated aqueous NaHCO3 (25 mL) was added to the solution and the mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (50 mL) and washed with 0.5 M HCl (3×20 mL), saturated aqueous NaHCO3 (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 ethyl acetate in hexanes yielded the desired product (0.26 g, 40%). 1H NMR (400 MHz CDCl3) δ 4.62 (m, 2H), 4.13 (m, 1H), 2.11 (m, 1H), 1.94 (m, 1H), 1.40 (d, 3H, J=6.2 Hz). Anal. Calcd. For C10H9F5O4S: C, 37.51; H, 2.83. Found: C, 37.70; H, 2.93.

Source