boron trifluoride diethyl etherate in dichloromethane 2.5 h; Heating;

boron trifluoride diethyl etherate in dichloromethane 1 h;

1: 71 percent / NaNO2, n-propyl nitrite / dimethylsulfoxide / 1.5 h / 50 - 52 °C 2: 77 percent / dimethylsulfoxide / 0.42 h 3: DIBALH / CH2Cl2 / 0.42 h / -5 - 0 °C 4: acetic acid 5: 82 percent / BF3*Et2O / CH2Cl2 / 1 h View Scheme

1: DIBALH / CH2Cl2 / 0.42 h / -5 - 0 °C 2: acetic acid 3: 82 percent / BF3*Et2O / CH2Cl2 / 1 h View Scheme

1: 77 percent / dimethylsulfoxide / 0.42 h 2: DIBALH / CH2Cl2 / 0.42 h / -5 - 0 °C 3: acetic acid 4: 82 percent / BF3*Et2O / CH2Cl2 / 1 h View Scheme

1: acetic acid 2: 82 percent / BF3*Et2O / CH2Cl2 / 1 h View Scheme