Cesium carbonate → Tert-butyl 2-((5-oxo-5,6,7,8-tetrahydronaphthalen-1-yl)oxy)acetate

Participants

Reaction Steps

To a stirred mixture of 5-hydroxy-3,4-dihydro-2H-naphthalen-1-one (10.0 g, 61.7 mmol) and cesium carbonate (58.5 g, 180 mmol) in acetonitrile (300 mL) was added tert-butyl bromoacetate (29.0 g, 148 mmol) at room temperature under nitrogen. After being stirred at room temperature overnight, the reaction mixture was filtered through a pad of Celite® (a diatomite filter), and washed with ethyl acetate (100 mL). The combined filtrates were concentrated under reduced pressure. The residue was partitioned between ethyl acetate (500 mL) and water (200 mL×3). The organic layer was concentrated under reduced pressure. Column chromatography (silica gel, 100-200 mesh, 5-10% ethyl acetate in hexane) gave (5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (12.1 g, 71%). MS cald. for C16H20O4 276, obsd. 277 [(M+H)+].

Provenance & Evidence