Cesium carbonate → HCID 86653232, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of p-fluorobenzaldehyde (6.15 mmol, 0.763 g) in dimethylformamide (20.5 mL) was added cesium carbonate (4.1 mmol, 1.33 g) and 38 (4.1 mmol, 0.819 g). This solution was heated to 90° C. and monitored with TLC. When complete, the reaction mixture was cooled to room temperature and filtered through a fritted funnel. The filtrate was then diluted with ethyl acetate (200 mL) and extracted with eight 15 mL portions of water and one 10 mL portion of brine. The organic layer was dried over magnesium sulfate, evaporated to dryness and purified with flash chromatography to yield 0.930 g (3.05 mmol) of the title product. 1H NMR (500 MHz, CDCl3) δ 9.93 (s, 1H), 7.85 (d, J=8.6, 2H), 7.55-7.22 (m, 6H), 7.07 (d, J=8.7, 2H), 6.86 (d, J=8.3, 1H), 6.71 (dd, J=5.2, 10.7, 2H), 5.06 (s, 2H). 13C NMR (126 MHz, CDCl3) δ 190.79, 162.93, 160.50, 156.39, 131.94, 130.61, 128.66, 128.15, 127.52, 117.78, 112.66, 111.44, 107.25, 70.18.

Provenance & Evidence