反应 #1973938

反应方程式

NaHCO3

ethyl acetate

3-methyl-1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

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

溶剂

—

hexanes

CH2Cl2

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 15 min
2. 2
   萃取The organics were extracted with CH2Cl2
3. 3
   洗涤washed with 0.5 M HCl (1×20 mL) and saturated aqueous NaCl (1×20 mL)
4. 4
   干燥The organics were dried over Na2SO4
5. 5
   浓缩concentrated
6. 6
   其他to give a crude mixture

实验过程

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.

来源