sulfuric acid in methanol

in methanol T=-20 - 50°C;

argentic oxide; nitric acid in 1,4-dioxane T=20°C;

1.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 1.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 2.1: 98 percent / KOtBu / toluene / 4 h / Heating 3.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 4.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 5.1: 98 percent / KOtBu / toluene / 3 h / Heating 6.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: 74 percent / HBr; AcOH / 16 h / 20 °C 2.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 2.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 3.1: 98 percent / KOtBu / toluene / 4 h / Heating 4.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 5.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 6.1: 98 percent / KOtBu / toluene / 3 h / Heating 7.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: 87 percent / ethyl-2-methyl-1,3-dioxolan; p-TsOH / CH2Cl2 / 48 h / 20 °C 2.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 2.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 3.1: 98 percent / KOtBu / toluene / 4 h / Heating 4.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 5.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 6.1: 98 percent / KOtBu / toluene / 3 h / Heating 7.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 1.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 2.1: 98 percent / KOtBu / toluene / 4 h / Heating 3.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 4.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 5.1: 98 percent / KOtBu / toluene / 3 h / Heating 6.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1: 98 percent / KOtBu / toluene / 4 h / Heating 2: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 3: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 4: 98 percent / KOtBu / toluene / 3 h / Heating 5: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 2: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 3: 98 percent / KOtBu / toluene / 3 h / Heating 4: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme

1.1: methanol / 20 - 22 °C 2.1: PbO2 / 20 - 22 °C 3.1: 96 percent / H2SO4 / methanol 4.1: 5.50 mg / NaBH4 / ethanol / 3 h / 0 °C 5.1: 4.9 mg / NaOH; NaHSO3 / ethanol / 4 h / 70 - 80 °C 6.1: 74 percent / HBr; AcOH / 16 h / 20 °C 7.1: Li; NH3 / tetrahydrofuran; H2O / 0.75 h / -78 - -33 °C 7.2: 76 percent / tetrahydrofuran; H2O / 2 h / Heating 8.1: 98 percent / KOtBu / toluene / 4 h / Heating 9.1: 100 percent / HCl / tetrahydrofuran / 12 h / 20 °C 10.1: 89 percent / H2; Et3N / 10percent Pd/C / methanol / 12 h / 20 °C 11.1: 98 percent / KOtBu / toluene / 3 h / Heating 12.1: 26 percent / AgO; HNO3 / dioxane / 20 °C View Scheme