Potassium Carbonate → HCID 9956212, compound

Participants

Reaction Steps

Under an atmosphere of nitrogen, a mixture of the crude phenol of Step F, above (5.0 g, 15.4 mmol), potassium carbonate (1.3 g, 9.8 mmol), 18-crown-6 (130 mg), and 2-chloromethyl quinoline (4.1 g, 23 mmol) in 50 mL of acetonitrile is stirred at 60° C. for 24 hours (TLC, silica, dichloromethane-MeOH 19:1). The solvent is evaporated and the residue partitioned between ethyl acetate and water (75 mL each). The insolubles are filtered, the layers separated and the organic phase washed with 1N NaOH and brine. After drying (MgSO4) the solvent is removed in vacuo to give 7.0 g of a thick brown oil. The crude product is purified by flash chromatography (silica Merck 60, dichloromethane and dichloromethane-ethyl acetate 19:1) to give the product (4.2 g, clear oil). The oil is triturated with ethanol to give crystalline product (3.98 g, 55.5%, m.p. 90°-91° C., white solid).

Provenance & Evidence