反応 #1973940

反応方程式

NaHCO3

ethyl acetate

3-methoxy-3-methylbutane-1-ol

pentafluorobenzenesulfonyl chloride

→

desired product

収率 163.0%

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

収率 163.0%

溶媒

—

hexanes

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 30 min
2. 2
   抽出The organics were extracted with CH2Cl2 (75 mL)
3. 3
   洗浄washed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL)
4. 4
   乾燥The organics were dried over Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他to give a crude mixture

実験手順

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.

出典