Sodium borohydride → 1-Cyano-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

Sodium borohydride (6.8 g) is added to a suspension of 6.1 g (23.3 mmol) of 1-cyano-5-methoxy-3-phenyl-3,4-dihydronaphthalene, from Step 1, in 100 mL of absolute ethanol and the reaction mixture is heated at reflux temperature for 1.5 h. The solvent is evaporated under reduced pressure and the residue partitioned between equal volumes of ethyl acetate and 1N aqueous hydrochloric acid solution. The layers are separated and the organic layer is washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound.

Provenance & Evidence