Réaction #1973937

Équation de réaction

3-methyl-1,3-butane diol

o-(trifluoromethyl)benzenesulfonyl chloride

ethyl acetate

→

desired product

Rendement 66.7%

3-Hydroxy-3-methylbutyl 2-(trifluoromethyl)benzenesulfonate

Rendement 66.7%

Solvants

CH2Cl2

CH2Cl2

CH2Cl2

—

hexanes

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 mL)
2. 2
   SéchageThe organics were dried over Na2SO4
3. 3
   Concentrationconcentrated
4. 4
   Autreto give a crude mixture

Mode opératoire

To a solution of 3-methyl-1,3-butane diol (2.5 g, 21 mmol) and TEA (1.63 g, 16 mmol) in CH2Cl2 (15 mL) was added o-(trifluoromethyl)benzenesulfonyl chloride (2.03 g, 8.3 mmol) dissolved in CH2Cl2 (20 mL). The solution was stirred at rt for 7 h. The reaction mixture was diluted with CH2Cl2 (75 mL) and washed with 1 M HCl (2×25 mL), saturated aqueous NaHCO3 (1×25 mL) and saturated aqueous NaCl (1×25 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 (1.73 g, 66%). 1H NMR (400 MHz CDCl3) δ 8.23 (m, 1H), 7.91 (m, 1H), 7.75 (m, 2H), 4.32 (t, 2H, J=7.0 Hz), 1.91 (t, 2H, J=7.0 Hz) 1.22 (s, 6H). Anal. Calcd. For C12H15F3O4S: C, 46.15; H, 4.84. Found: C, 45.73; H, 4.88.

Source