boron trifluoride diethyl etherate in dichloromethane T=-80°C; 8 h;

boron trifluoride diethyl etherate T=-80°C;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane 4 h; Ambient temperature;

1: 60 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 4 h / Ambient temperature 2: pyridine / 3 h / Ambient temperature 3: dicyclohexane-crown-6, KMnO4 / CH2Cl2 / 1) 15 deg C, 3 h, 2) room temp., 3 h 4: pyridine / 5 h / Ambient temperature 5: DIBALH / CH2Cl2 / 5 h / -80 °C 6: citric acid / methanol / 3 h / Ambient temperature 7: pyridine, DMAP / 5 h / Ambient temperature View Scheme

1: 60 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 4 h / Ambient temperature 2: pyridine / 3 h / Ambient temperature 3: dicyclohexane-crown-6, KMnO4 / CH2Cl2 / 1) 15 deg C, 3 h, 2) room temp., 3 h 4: pyridine / 5 h / Ambient temperature View Scheme

1: pyridine / 3 h / Ambient temperature 2: dicyclohexane-18-crown-6, KMnO4 / CH2Cl2 / 1) 15 deg C, 3 h, 2) room temp., 3 h 3: pyridine / 5 h / Ambient temperature 4: DIBALH / CH2Cl2 / 5 h / -80 °C 5: citric acid / methanol / 3 h / Ambient temperature 6: pyridine, DMAP / 5 h / Ambient temperature View Scheme