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

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)+].

1. filtrationthe reaction mixture was filtered through a pad of Celite® (a diatomite
2. filtrationfilter), and
3. washwashed with ethyl acetate (100 mL)
4. concentrationThe combined filtrates were concentrated under reduced pressure
5. customThe residue was partitioned between ethyl acetate (500 mL) and water (200 mL×3)
6. concentrationThe organic layer was concentrated under reduced pressure

ORD record

ord-f306c41e7d9f442baa7d292be0828072

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163781B2