dichloro bis(acetonitrile) palladium(II) in water; acetonitrile Heating;

hydrogen; nickel in methanol

1: 1) BuLi, 2) Me3Ga 2: pyridine / or Li-salt of the corresponding acetylenic alcohol 3: NaN3 / dimethylformamide / 4 h / 60 - 70 °C 4: LiAlH4 / diethyl ether / 0 °C 5: 72 percent / PdCl2(MeCN)2 / acetonitrile; H2O / Heating View Scheme

1: pyridine / or Li-salt of the corresponding acetylenic alcohol 2: NaN3 / dimethylformamide / 4 h / 60 - 70 °C 3: LiAlH4 / diethyl ether / 0 °C 4: 72 percent / PdCl2(MeCN)2 / acetonitrile; H2O / Heating View Scheme

sodium hydroxide; sodium hypochlorite Multistep reaction. Title compound not separated from byproducts;