Water → (E)-(6-methoxyindan-1-ylidene)acetonitrile

Participants

Reaction Steps

To a suspension of 60% sodium hydride (2.71 g, 67.9 mmol.) in tetrahydrofuran (150 ml) was added dropwise, under ice-cooling, diethyl cyanomethylphosphonate (11.5 g, 64.8 mmol.). The mixture was stirred for 15 minutes. To the reaction mixture was added dropwise a solution of 6-methoxy-1-indanone (10.0 g, 61.7 mmol.) in tetrahydrofuran (30 ml). The reaction mixture was stirred for 30 minutes at room temperature, which was poured into water, and then the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue thus obtained was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8), followed by recrystallization from ethyl acetate/hexane to afford the titled compound (6.00 g, yield 53%), m.p.95-96° C. (recrystallized from ethyl acetate/hexane).

Provenance & Evidence