Ethyl Acetate → 3-Methoxy-3-methylbutyl 2,2,2-trifluoroethanesulfonate

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).

1. extractionThe organics were extracted with CH2Cl2 (25 mL)
2. washwashed with 0.1 M HCl (3×20 mL), saturated aqueous NaHCO3 (1×20 mL) and saturated aqueous NaCl (1×20 mL)
3. dry with materialThe organics were dried over Na2SO4
4. concentrationconcentrated
5. customto give a crude mixture

ORD record

ord-88c00843b15e486b9c47c376ba700dcf

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501382B1