(i) Na, liq. NH3, (ii) /BRN= 1732408/, Et2O; Multistep reaction;

1: KI / acetone; H2O / Heating 2: (i) NaOEt, (ii) KOH, MeOH, H2O 3: (i) EtMgBr, THF, (ii) CuCN, /BRN= 1744118/ View Scheme

1: KI / acetone; H2O / Heating 2: (i) NaOEt, (ii) KOH, MeOH, H2O View Scheme

1: NaNH2 / diethyl ether 2: H2 / Lindlar catalyst / methanol 3: NaI / dimethylsulfoxide View Scheme

sodium amide in diethyl ether

1: NaNH2 / diethyl ether 2: H2 / Lindlar catalyst / methanol View Scheme

1: (i) EtMgBr, ether, THF, (ii) /BRN= 605309/, CuCl 2: (i) EtMgBr, ether, THF, (ii) /BRN= 1902461/, CuCl 3: H2, quinoline / Lindlar catalyst / pentane / 4 h / 15 °C View Scheme

1: H2 / Lindlar catalyst / ethyl acetate 2: NaI / acetone / 60 h / Heating View Scheme

1: tetrahydrofuran / 1 h / 60 - 70 °C 2: tetrahydrofuran; toluene / 20 h / 90 - 100 °C 3: 1.) Ni(II)(CH3COO)2, NBH4, ethylene diamine; 2.) H2 / 1.) ethanol, Rt, 30 min; 2.) ethanol, 5 kg/cm2, 20-30 deg C 4: 20percent HCl / CH2Cl2 / 1 h / Ambient temperature 5: 1.) t-BuOK; / 1.) THF, Rt, 30 min; 2.) THF, 10-20 deg C, 50 min; 3.) AcOH, 160 deg C, 7 hr View Scheme

1: KI / acetone; H2O / Heating 2: (i) NaOEt, (ii) KOH, MeOH, H2O 3: (i) EtMgBr, THF, (ii) CuCl, /BRN= 1922124/ View Scheme