반응 #1973942

반응 방정식

NaHCO3

ethyl acetate

1,3-butane diol

pentafluorobenzenesulfonyl chloride

→

desired product

수율 40.6%

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

수율 40.6%

용매

CH2Cl2

—

hexanes

CH2Cl2

반응 조건

후처리

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

실험 절차

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.

출처