in toluene 0.5 h; Heatingin the dark;

1: 90 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.67 h 2: 82 percent / NaOH / ethanol; H2O / 0.75 h / Ambient temperature 3: 78 percent / HCl / H2O / 40 °C 4: 84 percent / CAN / acetonitrile; H2O / 1 h / 0 °C 5: 1.) Cp2ZrCl2, 2.) NiCl2, PPh3, n-BuLi / 1.) ClCH2CH2Cl, 0 deg C, 2.) THF, hexane. -78 deg C, 30 min, -78 deg C to 0 deg C, 1.75 h View Scheme

1: 82 percent / NaOH / ethanol; H2O / 0.75 h / Ambient temperature 2: 78 percent / HCl / H2O / 40 °C 3: 84 percent / CAN / acetonitrile; H2O / 1 h / 0 °C 4: 1.) Cp2ZrCl2, 2.) NiCl2, PPh3, n-BuLi / 1.) ClCH2CH2Cl, 0 deg C, 2.) THF, hexane. -78 deg C, 30 min, -78 deg C to 0 deg C, 1.75 h View Scheme

1: 78 percent / HCl / H2O / 40 °C 2: 84 percent / CAN / acetonitrile; H2O / 1 h / 0 °C 3: 1.) Cp2ZrCl2, 2.) NiCl2, PPh3, n-BuLi / 1.) ClCH2CH2Cl, 0 deg C, 2.) THF, hexane. -78 deg C, 30 min, -78 deg C to 0 deg C, 1.75 h View Scheme

1: 80 percent / NaOMe / toluene / 2 h / Ambient temperature 2: 67 percent / K, t-BuOH, / toluene / 1 h / 0 °C 3: 99 percent / toluene / 0.5 h / Heating; in the dark View Scheme

1: 67 percent / K, t-BuOH, / toluene / 1 h / 0 °C 2: 99 percent / toluene / 0.5 h / Heating; in the dark View Scheme

boron trifluoride diethyl etherate; silver(l) oxide Yield given. Multistep reaction;

n-butyllithium; zirconocene dichloride; triphenylphosphine; nickel dichloride 1.) ClCH2CH2Cl, 0 deg C, 2.) THF, hexane. -78 deg C, 30 min, -78 deg C to 0 deg C, 1.75 h; Yield given. Multistep reaction;