反应 #1973940

反应方程式

NaHCO3

ethyl acetate

3-methoxy-3-methylbutane-1-ol

pentafluorobenzenesulfonyl chloride

→

desired product

收率 163.0%

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

收率 163.0%

溶剂

—

hexanes

CH2Cl2

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 30 min
2. 2
   萃取The organics were extracted with CH2Cl2 (75 mL)
3. 3
   洗涤washed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 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-methoxy-3-methylbutane-1-ol (1.07 g, 9 mmol) and TEA (0.61 g, 6 mmol) in CH2Cl2 (12 mL) was added pentafluorobenzenesulfonyl chloride (0.99 g, 3.7 mmol). The solution was stirred at rt for 2 h. Saturated aqueous NaHCO3 (12 mL) was added to the solution and the mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (75 mL) and washed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 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 (2.1 g, 81%). 1H NMR (400 MHz CDCl3) δ 4.42 (t, 2H, J=7.3 Hz), 3.13 (s, 3H), 1.97 (t, 2H, J=7.4 Hz), 1.17 (s, 6H); 19F NMR (400 MHz CDCl3) δ −137.9 (m, 2H), −146.65 (m, 1H), −161.01 (m, 2H). Anal. Calcd. For C12H13F5O4S: C, 41.38; H, 3.76. Found: C, 41.37; H, 3.77.

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