Sodium Iodide → HCID 11538196, compound

Participants

Reaction Steps

To a solution of 4-adamantan-1-yl-3-oxo-butyric acid ethyl ester, prepared by a modification of Wierenga and Skulnick's procedure (W. Wierenga and H. I. Skulnick, J. Org. Chem., 1979, 44, 310)(3.00 g, 11.0 mmol) in acetone (30 ml) was added sodium iodide (0.55 g, 3.67 mmol) and anhydrous potassium carbonate (3.04 g, 22.0 mmol), then a solution of 2-bromo-1-phenyl-ethanone (2.38 g, 11.5 mmol) in acetone (10 ml). The mixture was stirred at reflux for 36 h, cooled to room temperature and filtered. The filtrate was evaporated, the residue was dissolved in diethyl ether (50 ml) and washed with water (2×20 ml). The organic phase was dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, hexane/ethyl acetate 4:1) to afford the product as pale yellow oil (1.92 g, 46%). 1H NMR (300 MHz, CDCl3) 7.98 (2H, m), 7.65 (1H, m), 7.46 (2H, m), 4.19 (3H, m), 3.60 (1H, dd), 5.59 (1H, dd), 2.50 (2H, dd), 1.96 (3H, br s), 1.68 (12H, m), 1.29 (3H, t).

Provenance & Evidence