Ethanol → 1-Cycloperityl-3-(4-phenoxyphenyl)propane-1,3-dione

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Sodium hydride (1.508 g, 37.7 mmol, 60% suspension in mineral oil) was added in small portions to a solution of methyl cyclopentanecarboxylate (1.449 g, 11.31 mmol) and 1-(4-phenoxyphenyl)ethanone (2.00 g, 9.42 mmol) in THF (100 mL). Ethanol (0.5 mL) was then added. The mixture was heated to reflux for 5.5 h, quenched with saturated NaCl (50 mL) and acidified to pH 2 with 1 N HCl. THF was evaporated in vacuo. The residue was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (10 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with 5% ethyl acetate in hexanes and eluting with 5-20% ethyl acetate in hexanes, gave 1-cycloperityl-3-(4-phenoxyphenyl)propane-1,3-dione as white solid (1.837 g, 63% yield). MS (ES+) m/z: 309 (M+H); LC retention time: 5.015 min (analytical HPLC Method A).

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