1: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 2: pyridinium p-toluenesulfonate / methanol / 20 °C 3: aq. HCl / methanol / 0.25 h / 20 °C 4: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 2: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 3: pyridinium p-toluenesulfonate / methanol / 20 °C 4: aq. HCl / methanol / 0.25 h / 20 °C 5: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: 83 percent / KF; 18-crown-6 / dimethylformamide / 20 °C 2: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 3: pyridinium p-toluenesulfonate / methanol / 20 °C 4: aq. HCl / methanol / 0.25 h / 20 °C 5: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 2: pyridinium p-toluenesulfonate / methanol / 20 °C 3: aq. HCl / methanol / 0.25 h / 20 °C 4: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 2: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 3: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 4: pyridinium p-toluenesulfonate / methanol / 20 °C 5: aq. HCl / methanol / 0.25 h / 20 °C 6: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: 100 percent / Et3N / Lindlar catalyst / hexane / 0 - 20 °C 2: 54 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C 3: 50 percent / CrCl2 / tetrahydrofuran / 0 °C 4: CuI; NPrNH2 / Pd(PPh3)4 / benzene / 20 °C 5: pyridinium p-toluenesulfonate / methanol / 20 °C 6: aq. HCl / methanol / 0.25 h / 20 °C 7: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: aq. HCl / methanol / 0.25 h / 20 °C 2: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme

1: pyridinium p-toluenesulfonate / methanol / 20 °C 2: aq. HCl / methanol / 0.25 h / 20 °C 3: 70 percent / Zn(Cu/Ag) / aq. methanol / 5 h / 40 °C View Scheme