Cesium carbonate → HCID 21957496, compound

Participants

Reaction Steps

(1-Bromoethyl)benzene (0.56 mL, 4.13 mmol, 2 eq) was added to a stirred solution of 3-hydroxy-4-(2-phenylethoxy)-benzaldehyde (500 mg, 2.06 mmol, 1 eq) and cesium carbonate (672 mg, 2.06 mmol, 1 eq) in N,N-dimethylformamide (8 mL). The solution was stirred overnight and then diluted with ethyl acetate (50 mL). The organic solution was washed with 1M HCl (2×100 mL), and brine (100 mL), dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel and elution with petroleum ether:ethyl acetate (6:1) gave the product as a colourless oil (680 mg, 95%). RF (petroleum ether:ethyl actetate, 4:1) 0.51. 1H NMR (CDCl3) δ 9.72 (s, 1H, O═C—H), 6.93 (d, 1H, J 7.9 Hz, ArH), 5.38 (q, 1H, J 6.4 Hz, CHCH3Ph), 4.33 (m, 2H, CH2CH2Ph), 3.21 (t, 2H, J 6.8 Hz, CH2CH2Ph), 1.67 (d, 3H, J 6.4 Hz, CHCH3Ph).

Provenance & Evidence