Triethylamine → Ethyl(+/-)-4-(4,4,4-trifluoro-1-((methylsulfonyl)oxy)butyl)benzoate

Participants

Reaction Steps

To a solution of ethyl (+/−)-4-(4,4,4-trifluoro-1-hydroxybutyl)benzoate (264 mg, 0.956 mmol) in tert-butyl methyl ether (4.8 mL) was added triethylamine (0.201 mL, 1.43 mmol), followed by methanesulfonyl chloride (0.091 mL, 1.15 mmol). The resulting mixture was stirred for 1 hour. Then, the reaction mixture was diluted with tert-butyl methyl ether (25 mL) and washed with water (15 mL), sat. aq sodium bicarbonate (15 mL), then sat. aq sodium chloride (15 mL). The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give ethyl (+/−)-4-(4,4,4-trifluoro-1-((methylsulfonyl)oxy)butyl)benzoate. This material was used without further purification. 1HNMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 2 H), 7.48 (d, J=8.2 Hz, 2 H), 5.63 (dd, J=7.9, 4.8 Hz, 1 H), 4.41 (q, J=7.0 Hz, 2 H), 2.77 (s, 3 H), 2.39-2.08 (m, 4 H), 1.41 (t, J=7.1 Hz, 3 H).

Provenance & Evidence