1: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 2: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 3: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 4: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 5: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C View Scheme

methanol; potassium hydroxide; sodium perchlorate in tetrahydrofuran T=0 - 20°C; 3 - 4 h;

1: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 2: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C View Scheme

1: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 2: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 3: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 4: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 5: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 6: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 2: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 3: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature View Scheme