Réaction #1973944

Équation de réaction

NaHCO3

ethyl acetate

3-methoxybutane-1-ol

pentafluorobenzenesulfonyl chloride

→

desired product

Rendement 38.9%

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

Rendement 38.9%

Solvants

—

hexanes

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source