Sodium Hydroxide → HCID 22600576, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl trimethylammonium chloride (0.196 g, 1 mmol) was added to a solution of 2-phenylindene (0.200 g, 1.04 mmol) and α,α′-dibromoxylene (0.289 g, 1.09 mmol) in tetrahydrofuran (10 mL) then 50% aqueous sodium hydroxide (10 mL) was added. The resulting mixture was stirred at 50° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed sequentially with water, 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride then dried (MgSO4), filtered, and evaporated to a yellow solid. The crude product was purified by preparative thin layer chromatography on silica gel eluted with 98:2 hexane:ethyl acetate to afford 2-phenyl-1′,3′-dihydro-spiro[1H-indene-1,2′-[2H]indene] as a white amorphous solid (0.048 g). NMR (CDCl3, 500 MHz) δ 7.56 (2H, d, J=7 Hz), 7.42 (1H, d, J=7 Hz), 7.24-7.38 (9H, m, ArH), 7.09 (1H, t, J=7 Hz, ArH), 7.02 (1H, d, J=7 Hz, ArH), 3.78 (2H, d, J=16.5 Hz, CH2), 3.19 (2H, d, J=16.5 Hz, CH2).

Provenance & Evidence