Potassium Carbonate → Ethyl 7-(3-benzyloxypropoxy)-chromane-2-carboxylate

Participants

Reaction Steps

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. The aqueous layer was extracted with AcOEt twice. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on slica gel eluting with 10% AcOEt/hexanes to give the title compound 10.1 g (66%).

Provenance & Evidence