Reacción #1973942

Ecuación de reacción

NaHCO3

ethyl acetate

1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

Rendimiento 40.6%

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

Rendimiento 40.6%

Disolventes

CH2Cl2

—

hexanes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 30 min
2. 2
   ExtracciónThe organics were extracted with CH2Cl2 (50 mL)
3. 3
   Lavadowashed with 0.5 M HCl (3×20 mL), saturated aqueous NaHCO3 (1×20 mL) and saturated aqueous NaCl (1×20 mL)
4. 4
   SecadoThe organics were dried over Na2SO4
5. 5
   Concentraciónconcentrated
6. 6
   Otroto give a crude mixture

Procedimiento

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.

Fuente