1: 82 percent / 1.) BH3; 2.) <O>; 2: 60 percent / reagent Jones / acetone View Scheme

sodium hydride in N,N-dimethyl-formamide 16 h; Ambient temperature;

1: With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in toluene T=25°C; 2: With sodium hydroxide; bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride; isopropyl alcohol in toluene T=110°C; 2 h;

sodium hydride in N,N-dimethyl-formamide

in N-methyl-acetamide; mineral oil

1.1: 1.32 g / diethyl ether; cyclohexane / 3 h / 20 °C 2.1: NaH / tetrahydrofuran / 0.5 h / Heating 2.2: 81 percent / tetrahydrofuran / Heating 3.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 3.2: NaOH; 2-propanol; [Cl2(PCy3)2Ru=CHPh] / toluene / 2 h / 110 °C View Scheme

1.1: NaH / tetrahydrofuran / 0.5 h / Heating 1.2: 81 percent / tetrahydrofuran / Heating 2.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 2.2: NaOH; 2-propanol; [Cl2(PCy3)2Ru=CHPh] / toluene / 2 h / 110 °C View Scheme

1.1: NaH / tetrahydrofuran / 0.5 h / Heating 1.2: 53 percent / tetrahydrofuran / Heating 2.1: DIBAL-H / diethyl ether; cyclohexane / -90 °C 3.1: 1.32 g / diethyl ether; cyclohexane / 3 h / 20 °C 4.1: NaH / tetrahydrofuran / 0.5 h / Heating 4.2: 81 percent / tetrahydrofuran / Heating 5.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 5.2: NaOH; 2-propanol; [Cl2(PCy3)2Ru=CHPh] / toluene / 2 h / 110 °C View Scheme

1.1: DIBAL-H / diethyl ether; cyclohexane / -90 °C 2.1: 1.32 g / diethyl ether; cyclohexane / 3 h / 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / Heating 3.2: 81 percent / tetrahydrofuran / Heating 4.1: [Cl2(PCy3)2Ru=CHPh] / toluene / 25 °C 4.2: NaOH; 2-propanol; [Cl2(PCy3)2Ru=CHPh] / toluene / 2 h / 110 °C View Scheme

1: t-BuLi / tetrahydrofuran 2: 10.7 g / NaH / dimethylformamide / 16 h / 20 °C View Scheme