2,2,2-Trifluoroethanol → Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

Participants

Reaction Conditions

Reaction Steps

2,2,2-trifluoroethanol 7a (7.2 mL, 100 mmol) was dissolved in 300 mL dichloromethane, followed by addition of triethylamine (28 mL, 200 mmol). The reaction mixture was cooled to 0° C. The reaction mixture was warmed and stirred for 16 hours at room temperature after a solution (100 mL) of p-toluene sulfonyl chloride (TsCl) (30 g, 150 mmol) in dichloromethane was dropwise added. Thereafter, the reaction mixture was extracted with dichloromethane (100 mL×3) after 100 mL water were added. The organic extract was washed with saturated sodium chloride solution (50 mL) and combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system D to obtain the title compound 2,2,2-trifluoroethyl 4-methylbenzenesulfonate 7b (25 g, colourless liquid), yield: 98.4%. 1H NMR (400 MHz, CDCl3): δ 7.88-7.76 (m, 2H), 7.44-7.33 (m, 2H), 4.35 (d, 2H), 2.47 (s, 3H).

Provenance & Evidence