Ethyl Acetate → 3-Methoxybutyl 2,3,4,5,6-pentafluorobenzenesulfonate

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.

1. stirringthe mixture was stirred at rt for 30 min
2. extractionThe organics were extracted with CH2Cl2 (30 mL)
3. washwashed with 0.5 M HCl (2×20 mL) and saturated aqueous NaCl (1×20 mL)
4. dry with materialThe organics were dried over Na2SO4
5. concentrationconcentrated
6. customto give a crude mixture

ORD-Eintrag

ord-311afde7e0c54d5ca70e99ef09ee9b3a

Quelldatensatz

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08501382B1