Reacción #1973938

Ecuación de reacción

NaHCO3

ethyl acetate

3-methyl-1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

3-Hydroxy-3-methylbutyl 2,3,4,5,6-pentafluorobenzenesulfonate

Disolventes

—

hexanes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 15 min
2. 2
   ExtracciónThe organics were extracted with CH2Cl2
3. 3
   Lavadowashed with 0.5 M HCl (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 3-methyl-1,3-butane diol (0.79 g, 7.5 mmol) and TEA (0.37 g, 3.6 mmol) in CH2Cl2 (7 mL) at) 0° C. was added pentafluorobenzenesulfonyl chloride (0.80 g, 3.0 mmol). The solution was stirred at 0° C. for 1.5 h. Saturated aqueous NaHCO3 (10 mL) was added to the solution and the mixture was stirred at rt for 15 min. The organics were extracted with CH2Cl2 and washed with 0.5 M HCl (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 (30% ethyl acetate in hexanes) yielded the desired product as a white crystalline low melting point solid (0.69 g, 66%). 1H NMR (400 MHz CDCl3) δ 4.49 (t, 2H, J=7.0 Hz), 1.97 (t, 2H, J=7.0 Hz) 1.27 (s, 6H). Anal. Calcd. For C11H11F5O4S: C, 39.53; H, 3.32. Found: C, 39.54; H, 3.22.

Fuente