反应详情

To a 200 ml acetone solution of ethyl 7-hydroxychromane-2-carboxylate (9.18 g, 41.3 mmol) was added benzyl 3-bromopropyl ether (14.2 g, 62.0 mmol), powdered potassium carbonate (11.4 g, 82.5 mmol), and tetrabutylammonium iodide (1.53 g, 4 mmol). The resulting suspension was heated to reflux overnight. Acetone was removed under reduced pressure, diluted with AcOEt and sat. NH4Claq. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% AcOEt/hexanes to give the title compound 10.1 g (66%).

1. temperatureThe resulting suspension was heated
2. temperatureto reflux overnight
3. customAcetone was removed under reduced pressure
4. additiondiluted with AcOEt and sat. NH4Claq
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted twice with AcOEt
7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customchromatographed on silica gel eluting with 10% AcOEt/hexanes