triethylamine in dichloromethane 24 h; Heating;

1: aq. HCl, NaNO2 / 14 h / 0 - 20 °C 2: 1.) Ac2O / 1.) a) 55 deg C, 4 h, b) RT, 19 h, 2.) xylene, 120 deg C, 4 h 3: 77 percent / LiAlH4 / diethyl ether; CH2Cl2 / 2.5 h / Heating 4: 84 percent / Et3N / CH2Cl2 / 24 h / Heating View Scheme

1: 1.) Ac2O / 1.) a) 55 deg C, 4 h, b) RT, 19 h, 2.) xylene, 120 deg C, 4 h 2: 77 percent / LiAlH4 / diethyl ether; CH2Cl2 / 2.5 h / Heating 3: 84 percent / Et3N / CH2Cl2 / 24 h / Heating View Scheme

1: 77 percent / LiAlH4 / diethyl ether; CH2Cl2 / 2.5 h / Heating 2: 84 percent / Et3N / CH2Cl2 / 24 h / Heating View Scheme