Potassium Carbonate → Tert-butyl 4-(3-(4-(2,2,2-trifluoroethoxy)phenoxy)benzylidene)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 4-(3-(4-hydroxyphenoxy)benzylidene)piperidine-1-carboxylate (150 mg, 0.393 mmol) in dimethylformamide (5 mL) was treated with potassium carbonate (218 mg, 1.572 mmol), 18-crown ether (210 mg, 0.786 mmol) and 2-iodo-1,1,1 trifluoroethane (105 mg, 0.491 mmol). The mixture was stirred overnight at a temperature below 50° C. The reaction mixture was washed with water and organic part extracted with ether (2×50 mL). The organic fractions were dried over sodium sulfate and evaporated. The crude material was purified by column chromatography (10-20% ethyl acetate/hexanes) to give the title compound (50 mg, 27%). 1H-NMR (500 MHz, CDCl3): δ ppm 7.26 (m, 1H), 7.00 (d, J=6 Hz, 2H), 6.94 (m, 3H), 6.80 (m, 2H), 6.29 (s, 1H), 4.36 (m, 2H), 3.49 (s, 2H), 3.38 (s, 2H), 2.42 (s, 2H), 2.30 (s, 2H), 1.47 (s, 9H).

Provenance & Evidence