Реакция #1973942

Уравнение реакции

NaHCO3

ethyl acetate

1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

Выход 40.6%

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

Выход 40.6%

Растворители

CH2Cl2

—

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 (50 mL)
3. 3
   Промывкаwashed with 0.5 M HCl (3×20 mL), saturated aqueous NaHCO3 (1×20 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 1,3-butane diol (0.9 g, 10 mmol) and TEA (0.61 g, 6 mmol) in CH2Cl2 (4 mL) at 0° C. was added pentafluorobenzenesulfonyl chloride (0.53 g, 2 mmol) dissolved in CH2Cl2 (4 mL). The solution was stirred for 6 h over which time the solution slowly warmed to rt. Saturated aqueous NaHCO3 (25 mL) was added to the solution and the mixture was stirred at rt for 30 min. The organics were extracted with CH2Cl2 (50 mL) and washed with 0.5 M HCl (3×20 mL), saturated aqueous NaHCO3 (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 ethyl acetate in hexanes yielded the desired product (0.26 g, 40%). 1H NMR (400 MHz CDCl3) δ 4.62 (m, 2H), 4.13 (m, 1H), 2.11 (m, 1H), 1.94 (m, 1H), 1.40 (d, 3H, J=6.2 Hz). Anal. Calcd. For C10H9F5O4S: C, 37.51; H, 2.83. Found: C, 37.70; H, 2.93.

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