反応 #1973938

反応方程式

NaHCO3

ethyl acetate

3-methyl-1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

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

溶媒

—

hexanes

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 15 min
2. 2
   抽出The organics were extracted with CH2Cl2
3. 3
   洗浄washed with 0.5 M HCl (1×20 mL) and saturated aqueous NaCl (1×20 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-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.

出典