[Na].[H][H].CC(C)=O.[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23](=[O:25])[CH3:24])=[CH:17][CH:16]=1>C(O)C.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C.B#[Ni]>[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])=[CH:17][CH:16]=115 Gm (0.06 mol) of nickel(II)acetate tetrahydrate, dissolved in 600 ml of 95% ethanol, were reduced to black, colloidal nickel boride (P-2-catalyst) in a hydrogenation vessel with 60 ml of 1 M sodium borohyride solution in an atmosphere of hydrogen. In order to remove any unreacted borohydride which may be present, 14 gm (0.24 mol) of acetone were first added and the mixture was shaken for one hour at room temperature. Thereafter, 30.0 gm (0.123 mol) of (E)-4-(2'-fluoro-4-biphenylyl)-3-buten-2-one were added, and the mixture was hydrogenated at room temperature and 5 atmospheres until the absorption of hydrogen terminated. Subsequently, the catalyst was filtered off, the filtrate was evaporated in vacuo, and the residue was shaken with a mixture of water and ethyl acetate. The organic phase was dried over sodium sulfate and then evaporated, and the residue was distilled in a high vacuum, yielding 18.5 gm (62% of theory) of 4-(2'-fluoro-4-biphenylyl)-2-butanone in the form of a colorless, viscous oil having a boiling point of 153°-155°C at 0.4 mm Hg which solidified after prolonged standing and then had a melting point of 30°C.
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