反应详情

2,4-Dihydroxy-6-methyl-benzoic acid ethyl ester (315 mg, 1.6 mmol) is combined with 2-(3-chloromethyl-phenoxymethyl)-quinoline hydrochloride (0.51 g, 1.6 mmol, example 49), tetrabutylammonium iodide (55 mg, 0.15 mmol) and potassium carbonate (0.48 g, 3.5 mmol) in acetone (9 mL). The reaction is heated at reflux 48 h. The reaction is partitioned between ethyl acetate and saturated ammonium chloride. The organic phase is washed with brine, dried over magnesium sulfate, filtered and concentrated to yield the crude product. This material is purified by column chromatography (silica, 3% ether in dichloromethane) to the title compound; m.p. 127–128° C., MS (ESI) 444 (M+H)+.

1. temperatureThe reaction is heated
2. temperatureat reflux 48 h
3. customThe reaction is partitioned between ethyl acetate and saturated ammonium chloride
4. washThe organic phase is washed with brine
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated