sodium hydroxide in ethanol T=25°C;

1: 1.) LDA / 1.) - 78 deg C, 10 min 2.) -78 deg C, 1 h and warming to 25 deg C, 1 h. 2: 89 percent / tetrahydrofuran / 25 °C 3: 90 percent / NaBH4 / ethanol / 1 h / -30 °C 5: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 6: 1.) CuCN / 1.) -78 deg C, 1 h 2.) - 78 deg C, 1 h and -45 deg C, 14 h 7: 87 percent / MeOH, p-TsOH / 12 h / 25 °C 8: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 9: NaOH / aq. ethanol / 25 °C View Scheme

1: 89 percent / tetrahydrofuran / 25 °C 2: 90 percent / NaBH4 / ethanol / 1 h / -30 °C 4: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 5: 1.) CuCN / 1.) -78 deg C, 1 h 2.) - 78 deg C, 1 h and -45 deg C, 14 h 6: 87 percent / MeOH, p-TsOH / 12 h / 25 °C 7: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 8: NaOH / aq. ethanol / 25 °C View Scheme

2: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3: 1.) CuCN / 1.) -78 deg C, 1 h 2.) - 78 deg C, 1 h and -45 deg C, 14 h 4: 87 percent / MeOH, p-TsOH / 12 h / 25 °C 5: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 6: NaOH / aq. ethanol / 25 °C View Scheme

1: 90 percent / NaBH4 / ethanol / 1 h / -30 °C 3: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 4: 1.) CuCN / 1.) -78 deg C, 1 h 2.) - 78 deg C, 1 h and -45 deg C, 14 h 5: 87 percent / MeOH, p-TsOH / 12 h / 25 °C 6: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 7: NaOH / aq. ethanol / 25 °C View Scheme

1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 2: 1.) CuCN / 1.) -78 deg C, 1 h 2.) - 78 deg C, 1 h and -45 deg C, 14 h 3: 87 percent / MeOH, p-TsOH / 12 h / 25 °C 4: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 5: NaOH / aq. ethanol / 25 °C View Scheme

1: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 2: NaOH / aq. ethanol / 25 °C View Scheme

1: 87 percent / MeOH, p-TsOH / 12 h / 25 °C 2: 83 percent / hydrogen / 5percent Pd-CaCO3 / benzene / 25 °C / 760 Torr / cat. 10percent by weight 3: NaOH / aq. ethanol / 25 °C View Scheme