Реакция #1973944

Уравнение реакции

NaHCO3

ethyl acetate

3-methoxybutane-1-ol

pentafluorobenzenesulfonyl chloride

→

desired product

Выход 38.9%

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

Выход 38.9%

Растворители

—

hexanes

CH2Cl2

Условия реакции

Обработка

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

Методика

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.

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