potassium tert-butylate in tetrahydrofuran T=0°C; 1 h;

1: pyridine / 4 h / 50 °C 2: DIBAL-H / tetrahydrofuran / 2 h / -78 °C 3: thionyl chloride / CH2Cl2 / 2 h / 23 °C 4: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C 5: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 6: DBU / CH2Cl2 / 1 h / 0 °C 7: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

1: pyridine / 4 h / 50 °C 2: DIBAL-H / tetrahydrofuran / 2 h / -78 °C 3: thionyl chloride / CH2Cl2 / 2 h / 23 °C 4: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C 5: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 6: DBU / CH2Cl2 / 1 h / 0 °C 7: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

1: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 2: DBU / CH2Cl2 / 1 h / 0 °C 3: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

1: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C 2: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 3: DBU / CH2Cl2 / 1 h / 0 °C 4: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

1: thionyl chloride / CH2Cl2 / 2 h / 23 °C 2: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C 3: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 4: DBU / CH2Cl2 / 1 h / 0 °C 5: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

1: DIBAL-H / tetrahydrofuran / 2 h / -78 °C 2: thionyl chloride / CH2Cl2 / 2 h / 23 °C 3: potassium t-butoxide / tetrahydrofuran / 1 h / -78 °C 4: N-iodosuccinimide / tetrahydrofuran / 2 h / -15 °C 5: DBU / CH2Cl2 / 1 h / 0 °C 6: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

1: DBU / CH2Cl2 / 1 h / 0 °C 2: 82 percent / potassium t-butoxide / tetrahydrofuran / 1 h / 0 °C View Scheme

in pyridine

sodium methylate in methanol T=23°C; 4 h;