Reaction #1973945

Reaction equation

3-methoxy-3-methylbutane-1-ol

2,2,2-trifluoroethanesulfonyl chloride

ethyl acetate

→

desired product

Yield 50.0%

3-methoxy-3-methylbutyl 2,2,2-trifluoroethanesulfonate

Yield 50.0%

Solvents

CH2Cl2

—

hexanes

Conditions

Workup

1. 1
   ExtractionThe organics were extracted with CH2Cl2 (25 mL)
2. 2
   Washwashed with 0.1 M HCl (3×20 mL), saturated aqueous NaHCO3 (1×20 mL) and saturated aqueous NaCl (1×20 mL)
3. 3
   DryingThe organics were dried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   Otherto give a crude mixture

Procedure

To a solution of 3-methoxy-3-methylbutane-1-ol (0.4 g, 3.4 mmol) and TEA (0.2 g, 2 mmol) in CH2Cl2 (6 mL) was added 2,2,2-trifluoroethanesulfonyl chloride (0.12 g, 0.66 mmol). The solution was stirred at rt for 1 h. The organics were extracted with CH2Cl2 (25 mL) and washed with 0.1 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 as an oil (0.086 g, 50%). 1H NMR (400 MHz CDCl3) δ 4.41 (t, 2H, J=7.3 Hz), 3.87 (q, 2H, J=8.8 Hz), 3.14 (s, 3H), 1.94 (t, 2H, J=7.3), 1.16 (s, 6H).

Source