(i) SOCl2, (ii) /BRN= 5645542/, benzene, (iii) /BRN= 3592982/; Multistep reaction;

3 h; Heating;

1: pentan-2-one; potassium carbonate / Behandeln des Reaktionsprodukts in Benzol mit wss.-methanol. Kalilauge 2: hydrazine hydrate; potassium hydroxide; triethylene glycol / 200 °C View Scheme

1: potassium carbonate; pentan-2-one / Erwaermen des Reaktionsprodukts mit wss.-methanol. Kalilauge View Scheme

1,4-dioxane; methanol; nickel T=100°C; P=73550.8 Torr; Hydrogenation.und Erwaermen des Reaktionsprodukts mit aethanol.Kalilauge;

1: 97 percent / 4-(dimethylamino)pyridine / toluene / 40 h / Heating 2: 76 percent / diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / 1.) toluene, -78 deg C, 30min, 2.) -60 deg C, 1.5 h 3: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature 4: 89 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2 h / 0 °C 5: 96 percent / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) reflux, 3 h 6: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenyl phosphorazidate / tetrahydrofuran / 24 h 7: 2.) LiAlH4 / 1.) o-dichlorobenzene, 165 deg C, 2.5 h, 2.) THF, toluene, -78 deg C to 0 deg C, 3.5 h View Scheme

1: 42 percent / Ru-(+)-BINAP 2: HOBT-Ms; TEA / tetrahydrofuran View Scheme