pyridinium chlorochromate in dichloromethane T=20°C; 3 h;

1: 95 percent / NaH / tetrahydrofuran 2: 76 percent / 4N HCl / tetrahydrofuran / 6 h / Ambient temperature 3: potassium hydroxide / methanol 4: 85 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 160 - 165 °C 5: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 6: 74 percent / pyridinium chlorochromate View Scheme

1: lithium aluminium hydride 2: 95 percent / NaH / tetrahydrofuran 3: 76 percent / 4N HCl / tetrahydrofuran / 6 h / Ambient temperature 4: potassium hydroxide / methanol 5: 85 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 160 - 165 °C 6: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 7: 74 percent / pyridinium chlorochromate View Scheme

1: potassium hydroxide / methanol 2: 85 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 160 - 165 °C 3: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 4: 74 percent / pyridinium chlorochromate View Scheme

1: 76 percent / 4N HCl / tetrahydrofuran / 6 h / Ambient temperature 2: potassium hydroxide / methanol 3: 85 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 160 - 165 °C 4: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 5: 74 percent / pyridinium chlorochromate View Scheme

1: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 2: 74 percent / pyridinium chlorochromate View Scheme

1: 85 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 160 - 165 °C 2: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 3: 74 percent / pyridinium chlorochromate View Scheme

1: 85 percent / potassium hydroxide / methanol 2: 85 percent / Cu, pyridine / bis-(2-hydroxy-ethyl) ether / 160 - 165 °C 3: 96 percent / boron tribromide / CH2Cl2 / -70 deg C to 20 deg C 4: 74 percent / pyridinium chlorochromate View Scheme