sodium hydroxide in ethanol; water 2 h; Heating;

1: 62 percent / 0.17 h / 85 - 90 °C 2: 67 percent / NaBH4 / ethanol / 2 h / Heating 3: pyridine / 12 h / Ambient temperature 4: 65 percent / conc. HCl / dioxane / 2 h / Heating 5: 97 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 90 °C 6: 70 percent / CH2Cl2; H2O / ice cooling, 1.5 h, then Rt, 18 h 7: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 8: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme

1: 70 percent / CH2Cl2; H2O / ice cooling, 1.5 h, then Rt, 18 h 2: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 3: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme

1: 67 percent / NaBH4 / ethanol / 2 h / Heating 2: pyridine / 12 h / Ambient temperature 3: 65 percent / conc. HCl / dioxane / 2 h / Heating 4: 97 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 90 °C 5: 70 percent / CH2Cl2; H2O / ice cooling, 1.5 h, then Rt, 18 h 6: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 7: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme

1: pyridine / 12 h / Ambient temperature 2: 65 percent / conc. HCl / dioxane / 2 h / Heating 3: 97 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 90 °C 4: 70 percent / CH2Cl2; H2O / ice cooling, 1.5 h, then Rt, 18 h 5: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 6: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme

1: 97 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 90 °C 2: 70 percent / CH2Cl2; H2O / ice cooling, 1.5 h, then Rt, 18 h 3: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 4: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme

1: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 2: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme

1: 65 percent / conc. HCl / dioxane / 2 h / Heating 2: 97 percent / t-BuOK / 2-methyl-propan-2-ol / 2 h / 90 °C 3: 70 percent / CH2Cl2; H2O / ice cooling, 1.5 h, then Rt, 18 h 4: 57 percent / 1.) NaH / dimethylformamide / 0.5 h / -8 - 22 °C 5: 85 percent / NaOH / ethanol; H2O / 2 h / Heating View Scheme