Acetonitrile → HCID 10858248, compound

Participants

Reaction Steps

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (2.19 g, 13.6 mmol.) in tetrahydrofuran (80 ml) was gradually added dropwise, under argon atmosphere at -78° C., a normal butyl lithium hexane solution (1.56 M, 8.72 ml, 13.6 mmol.). The mixture was stirred for 10 minutes, to which was then added dropwise acetonitrile (0.65 ml, 12.4 mmol.). The mixture was stirred for further 20 minutes, to which was added dropwise a solution of 6-methoxy-2-phenyl-1-indanone (2.70 g, 11.3 mmol.) in tetrahydrofuran (10 ml), and the mixture was stirred for one hour. The temperature of the reaction mixture was gradually reverted to room temperature while pouring water thereto, and the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was dissolved in toluene (100 ml), to which was added 10-camphor-sulfonic acid (0.5 g). The reaction mixture was heated for 2 hours under reflux. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, and the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue thus obtained was recrystallized to afford the titled compound (yield 0.47 g, yield 16%).

Provenance & Evidence