반응 #1973941

반응 방정식

NaHCO3

ethyl acetate

1,3-butane diol

o-(trifluoromethyl)benzenesulfonyl chloride

→

desired product

수율 84.0%

3-Hydroxybutyl 2-(trifluoromethyl)benzenesulfonate

수율 84.0%

용매

CH2Cl2

—

hexanes

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGwas stirred at rt for 45 min
2. 2
   추출The organics were extracted with CH2Cl2 (150 mL)
3. 3
   세척washed with 0.5 M HCl (2×80 mL) and saturated aqueous NaCl (1×50 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 (2.18 g, 24 mmol) and TEA (1.64 g, 16 mmol) in CH2Cl2 (15 mL) at 0° C. was added o-(trifluoromethyl)benzenesulfonyl chloride (2 g, 8 mmol) dissolved in CH2Cl2 (20 mL). The solution was stirred at 0° C. for 2 h. Saturated aqueous NaHCO3 (15 mL) was added to the solution and mixture was stirred at rt for 45 min. The organics were extracted with CH2Cl2 (150 mL) and washed with 0.5 M HCl (2×80 mL) and saturated aqueous NaCl (1×50 mL). The organics were dried over Na2SO4 and concentrated to give a crude mixture. Silica gel chromatography (50% ethyl acetate in hexanes) yielded the desired product (2 g, 84%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.92 (m, 1H), 7.74 (m, 2H), 4.34 (m, 1H), 4.24 (m, 1H), 3.95 (m, 1H), 1.89 (m, 1H), 1.73 (m, 1H), 1.20 (d, 3H, J=6.3 Hz). Anal. Calcd. For C11H13F3O4S: C, 44.29; H, 4.39. Found: C, 44.29; H, 4.28.

출처