PbO T=260 - 270°C;

1: 55 percent / tetrahydrofuran / 2 h / Ambient temperature 2: 56 percent / POCl3 / pyridine / 0.17 h / Heating View Scheme

chromium; acetic acid T=100°C;

chromium(VI) oxide; acetic acid

1: dimethylformamide / 20 °C 2: 1.022 g / aq. NaOH; methanol / 20 °C 3: NaBH4; I2 / tetrahydrofuran / 0.33 h / 20 °C 4: 1.81 g / PCC / CH2Cl2 / 3 h / 20 °C 5: potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C 6: 155 mg / aq. HCl / tetrahydrofuran; 2-methyl-propan-2-ol; methanol / 1 h / 20 °C View Scheme

1: 1.81 g / PCC / CH2Cl2 / 3 h / 20 °C 2: potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C 3: 155 mg / aq. HCl / tetrahydrofuran; 2-methyl-propan-2-ol; methanol / 1 h / 20 °C View Scheme

1: 1.022 g / NBS; benzoyl peroxide / CCl4 / 1.5 h / Heating 2: dimethylformamide / 20 °C 3: 1.022 g / aq. NaOH; methanol / 20 °C 4: NaBH4; I2 / tetrahydrofuran / 0.33 h / 20 °C 5: 1.81 g / PCC / CH2Cl2 / 3 h / 20 °C 6: potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C 7: 155 mg / aq. HCl / tetrahydrofuran; 2-methyl-propan-2-ol; methanol / 1 h / 20 °C View Scheme

1: NaBH4; I2 / tetrahydrofuran / 0.33 h / 20 °C 2: 1.81 g / PCC / CH2Cl2 / 3 h / 20 °C 3: potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C 4: 155 mg / aq. HCl / tetrahydrofuran; 2-methyl-propan-2-ol; methanol / 1 h / 20 °C View Scheme

1: potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C 2: 155 mg / aq. HCl / tetrahydrofuran; 2-methyl-propan-2-ol; methanol / 1 h / 20 °C View Scheme

1: 1.022 g / aq. NaOH; methanol / 20 °C 2: NaBH4; I2 / tetrahydrofuran / 0.33 h / 20 °C 3: 1.81 g / PCC / CH2Cl2 / 3 h / 20 °C 4: potassium tert-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C 5: 155 mg / aq. HCl / tetrahydrofuran; 2-methyl-propan-2-ol; methanol / 1 h / 20 °C View Scheme