Cesium carbonate → HCID 68430453, compound

Participants

Reaction Steps

Add 4-chloromethyl-N-(4-cyano-phenyl)-benzamide (1.00 g, 3.69 mmol) to a solution of 1-(2,4-dihydroxy-3-propyl-phenyl)-ethanone (717 mg, 3.69 mmol) in dimethylformamide (14 mL). After 10 minutes add potassium carbonate (766 mg, 5.54 mmol) and cesium carbonate (1.204 g, 3.69 mmol). Stir at room temperature for one hour, then heat to 70° C. for 1.5 hours. Cool, and partition between ethyl acetate (100 mL) and water (100 mL). The organic phase is washed twice with water, brine, dried, and concentrated to dryness. The resulting residue is purified by silica gel column chromatography, eluting with 1:1 hexane:ethyl acetate to afford the title compound (820 mg, 52%): 1H NMR (CDCl3) δ 0.97 (t, 3H), 1.58 (m, 2H), 2.56 (s, 3H), 2.73 (m, 2H), 5.25 (s, 2H), 6.46 (d, 1H), 7.56-7.60 (m, 3H), 7.68 (d, 2H), 7.79 (d, 2H), 7.88-7.94 (m, 3H), 12.77 (s, 1H).

Provenance & Evidence