反応 #1973941

反応方程式

NaHCO3

ethyl acetate

1,3-butane diol

o-(trifluoromethyl)benzenesulfonyl chloride

→

desired product

収率 84.0%

3-Hydroxybutyl 2-(trifluoromethyl)benzenesulfonate

収率 84.0%

溶媒

CH2Cl2

—

hexanes

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGwas stirred at rt for 45 min
2. 2
   抽出The organics were extracted with CH2Cl2 (150 mL)
3. 3
   洗浄washed with 0.5 M HCl (2×80 mL) and saturated aqueous NaCl (1×50 mL)
4. 4
   乾燥The organics were dried over Na2SO4
5. 5
   濃縮concentrated
6. 6
   その他to give a crude mixture

実験手順

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.

出典