potassium hydroxide in methanol; water Hydrolysis;

1: 76 percent / imidazole; Ph3P; I2 / benzene / 3 h / 20 °C 2: 69 percent / NaH; BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / 20 °C 3: 73 percent / NaBH4 / methanol / 2 h / -30 - -25 °C 4: 82 percent / KOH / methanol; H2O View Scheme

1: 73 percent / NaBH4 / methanol / 2 h / -30 - -25 °C 2: 82 percent / KOH / methanol; H2O View Scheme

1.1: Et3N / CHCl3 / 12 h / 20 °C 1.2: 20 percent HCl / CHCl3 / 5 h / Heating 1.3: 76 percent / NaOH / H2O / 1 h / Heating 2.1: 46 percent / N2H4*H2O; KOH / bis-(2-hydroxy-ethyl) ether / 15 h / Heating 3.1: 74 percent / LiAlH4 / diethyl ether / 0.5 h / Heating 4.1: 76 percent / imidazole; Ph3P; I2 / benzene / 3 h / 20 °C 5.1: 69 percent / NaH; BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / 20 °C 6.1: 73 percent / NaBH4 / methanol / 2 h / -30 - -25 °C 7.1: 82 percent / KOH / methanol; H2O View Scheme

1: 69 percent / NaH; BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / 20 °C 2: 73 percent / NaBH4 / methanol / 2 h / -30 - -25 °C 3: 82 percent / KOH / methanol; H2O View Scheme