Cesium carbonate → 1-allyl-1-methyl-3,4-dihydronaphthalen-2(1H)-one

Participants

Reaction Steps

To a solution of 1-methyl-2-tetralone (10.0 g, 62.4 mmol), allyl acetate (7.42 mL, 68.7 mmol), cesium carbonate (20.3 g, 62.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.143 g, 0.156 mmol), 1,2-diaminocyclohexane-N,N′-bis(2′-diphenylphosphinobenzoyl) (0.215 g, 0.312 mmol) in tetrahydrofuran (300 mL) was bubbled a stream of nitrogen through the mixture for ten minutes. The solution was then stirred at room temperature for 4 days followed by the addition of ethyl acetate (200 mL) and a saturated aqueous solution of ammonium chloride. The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography employing 70-230 mesh silica gel eluting with a mixture of 10% ethyl acetate in hexane to provide the title compound as a light yellow oil (10.07 g, 90%). 1H NMR (300 MHz, CDCl3): δ 1.43 (s, 3 H), 2.46 m, 1 H), 2.63 m, 2 H), 2.78 m, 1 H), 3.03 m, 2 H), 4.90 m, 2 H), 5.40 m, 1 H), 7.18 (m, 2 H), 7.30 m, 2 H).

Provenance & Evidence