tetrabutyl ammonium fluoride in tetrahydrofuran T=25°C; 0.25 h;

1: diisobutylaluminum hydride / hexane; toluene / 1 h / 25 °C 2: imidazole / dimethylformamide / 1 h / 25 °C 3: 45 percent / tetra-n-butylammonium periodate / CH2Cl2 / 1 h / 25 °C 4: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C View Scheme

1: oxalyl chloride, DMF / tetrahydrofuran / 18 h / 25 °C 2: pyridine / tetrahydrofuran / 1 h / 25 °C 3: diisobutylaluminum hydride / hexane; toluene / 1 h / 25 °C 4: imidazole / dimethylformamide / 1 h / 25 °C 5: 45 percent / tetra-n-butylammonium periodate / CH2Cl2 / 1 h / 25 °C 6: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C View Scheme

1: 45 percent / tetra-n-butylammonium periodate / CH2Cl2 / 1 h / 25 °C 2: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C View Scheme

1: imidazole / dimethylformamide / 1 h / 25 °C 2: 45 percent / tetra-n-butylammonium periodate / CH2Cl2 / 1 h / 25 °C 3: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C View Scheme

1: pyridine / tetrahydrofuran / 1 h / 25 °C 2: diisobutylaluminum hydride / hexane; toluene / 1 h / 25 °C 3: imidazole / dimethylformamide / 1 h / 25 °C 4: 45 percent / tetra-n-butylammonium periodate / CH2Cl2 / 1 h / 25 °C 5: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 25 °C View Scheme