Chloride → 3,4-Dihydro-6-(2-thienyl)-1(2H)-naphthalenone

Participants

Reaction Conditions

Reaction Steps

3,4-Dihydro-6-trifluoromethylsulfonyloxy-1(2H)-naphthalenone (3.96 g, 13.5 mmol) was dissolved in 40 ml of N,N-dimethylformamide in an argon atmosphere, and 6.03 g (16.1 mmol) of 2-thienyltributyltin, 1.71 g (40.4 mmol) of lithium chloride and 0.47 g (0.67 mmol) of bistriphenylphosphinepalladium chloride were added to the solution. The mixture was stirred at 120° C. for 4 hours. The reaction product was cooled to room temperature. Ethyl acetate and a 2M-ammonium fluoride aqueous solution were added thereto, followed by stirring the mixture at room temperature overnight. The precipitate was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica-gel column chromatography (eluent: a mixture of 20% ethyl acetate and hexane) to obtain 2.44 g of the above-mentioned compound (yield 79%). NMR (CDCl3) δ (ppm): 8.04(1H, d, J=8 Hz), 7.57-7.35(4H, m), 7.13-7.11(1H, m), 2.99(2H, t, J=6 Hz), 2.67(2H, t, J=6 Hz), 2.21-2.11 (2H, m) MS (m/e): 228 (M+), 200

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