triethylamine in dichloromethane 24 h; Heating;

1: 1.) conc. aq. HCl, NaNO2, 2.) aq. AcONa / 1.) EtOH, 2.) EtOH, 4 h 2: 1.) NaOEt / 1.) EtOH, 1.5 h, 2.) EtOH, a) RT, 22 h, b) reflux, 10 min 3: 80 percent / LiAlH4 / diethyl ether / 1 h / Heating 4: 93 percent / Et3N / CH2Cl2 / 24 h / Heating View Scheme

1: 80 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 93 percent / Et3N / CH2Cl2 / 24 h / Heating View Scheme

1: 1.) NaOEt / 1.) EtOH, 1.5 h, 2.) EtOH, a) RT, 22 h, b) reflux, 10 min 2: 80 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 93 percent / Et3N / CH2Cl2 / 24 h / Heating View Scheme