Dimethyl Sulfoxide → 4-(3-Cyanopropyl)-6-methoxy-1,2-dihydronaphthalene

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A mixture of 4-(3-bromopropyl)-6-methoxy-1,2-dihydronaphthalene (10 g, 35.6 mmol), sodium cyanide (1.92 g, 39.1 mmol) and dimethyl sulfoxide (20 ml) was stirred for 1 hour at room temperature. The mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with brine and water, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to afford the titled compound (7.5 g, yield 93%, oil).

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