1: 80 percent / NaI / tetrahydrofuran / 10 h 2: 1.10 g / tetrabutyl ammonium bromide, aq. NaOH / CH2Cl2 / 1.) 0 deg C, 3 h, 2.) room temperature, 6 h 3: 1.) NaH / 1.) ether, -5-0 deg C, 10 min, 2.) ether, 10-15 deg C, 3 h 4: conc. HCl / CH2Cl2; diethyl ether / 0.25 h / 20 °C 5: 85 percent / 0.5N NaOH / ethanol / 6.5 h / Heating View Scheme

lithium chloride in acetone

1: 97 percent / alumina / benzene / 16 h / Heating 2: 83 percent / 25percent aq. NaOH / methanol / 16 h / Heating 3: 60 percent / LiAlH4 / diethyl ether / 0.5 h / Heating View Scheme

triethylamine in dichloromethane 0.5 h; Ambient temperature;

1: 75 percent / H2 / PII Nickel / ethanol / 760 Torr 2: triethylamine / CH2Cl2 / 2 h / Ambient temperature View Scheme