Reaktion #1973942

Reaktionsgleichung

NaHCO3

ethyl acetate

1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

Ausbeute 40.6%

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

Ausbeute 40.6%

Lösungsmittel

CH2Cl2

—

hexanes

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 30 min
2. 2
   ExtraktionThe organics were extracted with CH2Cl2 (50 mL)
3. 3
   Waschenwashed with 0.5 M HCl (3×20 mL), saturated aqueous NaHCO3 (1×20 mL) and saturated aqueous NaCl (1×20 mL)
4. 4
   TrocknenThe organics were dried over Na2SO4
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give a crude mixture

Vorschrift

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.

Quelle