1: 1-(tetrahydropyran-2-yloxy)-4-pentyne With ammonia; lithium; iron nitrate (III) in diethyl ether T=-70°C; 1 h; Inert atmosphere; 2: oxirane in diethyl ether Inert atmosphere;

n-butyllithium; benzophenone; CaH2; sodium in tetrahydrofuran; hexane

1: 96 percent / p-toluenesulfonic acid / tetrahydrofuran / Ambient temperature 2: 1.) n-butyllithium, HMPA / 1.) THF, hexane, -78 deg C 2.) -78 deg C to room temp. View Scheme

1: 96 percent / p-toluenesulfonic acid / tetrahydrofuran / Ambient temperature 2: 1.) n-butyllithium, HMPA / 1.) THF, hexane, -78 deg C 2.) -78 deg C to room temp. View Scheme

diethyl ether

ammonia; sodium amide; trichlorophosphate Reagens Nr. 4: Aether;

1: methanol; toluene-4-sulfonic acid 2: Raney nickel; methanol / 22065.2 - 36775.4 Torr / Hydrogenation View Scheme

1: methanol; toluene-4-sulfonic acid 2: Raney nickel; methanol / 22065.2 - 36775.4 Torr / Hydrogenation 3: pyridine; thionyl chloride View Scheme

1: 86 percent / pyridinium p-toluene sulfonate / aq. ethanol / 5 h / 53 - 58 °C 2: 97 percent / triethylamine / CH2Cl2 / 0.25 h 3: 70 percent / NaN3 / dimethylsulfoxide 4: triphenylphosphine, boiling stones / tetrahydrofuran; H2O / Ambient temperature 5: LiAlH4 / tetrahydrofuran / 18 h / Heating View Scheme