반응 #1973944

반응 방정식

NaHCO3

ethyl acetate

3-methoxybutane-1-ol

pentafluorobenzenesulfonyl chloride

→

desired product

수율 38.9%

3-Methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate

수율 38.9%

용매

—

hexanes

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 30 min
2. 2
   추출The organics were extracted with CH2Cl2 (30 mL)
3. 3
   세척washed with 0.5 M HCl (2×20 mL) and saturated aqueous NaCl (1×20 mL)
4. 4
   건조The organics were dried over Na2SO4
5. 5
   농축concentrated
6. 6
   기타to give a crude mixture

실험 절차

To a solution of 3-methoxybutane-1-ol (0.78 g, 7.5 mmol) and TEA (0.388 g, 3.8 mmol), in CH2Cl2 (15 mL) was added pentafluorobenzenesulfonyl chloride (0.79 g, 3.0 mmol). The solution was stirred at rt for 4 h. Saturated aqueous NaHCO3 (10 mL) was added to the solution and the mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (30 mL) and washed with 0.5 M HCl (2×20 mL) and saturated aqueous NaCl (1×20 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography (15% ethyl acetate in hexanes) yielded the desired product (0.39 g, 36%). 1H NMR (400 MHz CDCl3) δ 4.40 (m, 2H), 3.45 (m, 1H), 3.26 (s, 3H), 1.87 (m, 2H), 1.15 (d, 3H, J=6.1 Hz). Anal. Calcd. For C11H11F5O4S: C, 39.53; H, 3.32. Found: C, 39.83; H, 3.45.

출처