Potassium Carbonate → HCID 68576107, compound

Participants

Reaction Steps

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.5 g, 7.39 mmol), 1-bromo-4-chlorobutane (1.7 ml, 14.77 mmol), DMF (20 ml) and K2CO3 (4.1 g, 29.56 mmol) were reacted together according to general procedure E. Purification by chromatography on silica, eluant ethyl acetate:heptanes (33:66) provided a mixture of bromo and chloro phenoxy ether (1.3 g, 60%) which was used in the next stage. A portion of the mixture (0.5 g, 1.70 mmol) and pyrrolidine (0.42 ml, 5.11 mmol) were refluxed in EtOH (5 ml, 10 vol) overnight. The reaction was concentrated in vacuo and partitioned between 2M NaOH (10 ml) and ethyl acetate (10 ml). The aqueous was extracted with ethyl acetate (3×10 mL). The combined ethyl acetate layers were washed with brine (3×10 ml), dried over MgSO4, filtered, washed with ethyl acetate and concentrated in vacuo. Purification by chromatography on silica, eluant DCM:MeOH:NH3 (95:4:1) increasing gradually to DCM:MeOH:NH3 (93:6:1), gave the title compound as a pale yellow solid (350 mg, 63%). 1H NMR (400 MHz, DMSO-d6) δ 7.38 (d, 2H), 6.92 (d, 2H), 4.11-4.03 (m, 2H), 3.99 (t, 2H), 3.89 (td, 2H), 2.58-2.43 (m, 6H), 2.15-1.99 (m, 4H), 1.89-1.64 (m, 8H).

Provenance & Evidence