Potassium Carbonate → HCID 66816405, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(3-hydroxyphenyl)thiazole-4-carboxylate (24), (223 mg, 0.95 mmol, 1 eq.) and 2-(5-bromopentyloxy)tetrahydro-2H-pyran (357 mg, 1.42 mmol, 1.5 eq) in DMF (3 mL) was added powdered potassium carbonate (392 mg, 2.84 mmol, 3.0 eq.) The mixture was stirred vigorously for 4 h at 70° C., then concentrated in vacuo. The residue was diluted with ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (ethyl acetate:hexanes gradient). Yield 250 mg (65%). TLC Rf=0.44 (ethyl acetate:hexanes 3:7), MS m/z 322 (M+H)+

Provenance & Evidence