hydrogenchloride 3 h; Ambient temperature;

ammonia; sodium in tetrahydrofuran T=-78°C;

1: 95 percent / Na, liq. NH3 / tetrahydrofuran / -78 °C 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, 0 deg C, 30 min 3: 1.) NaH / 1.) THF, RT, 2.) THF, RT, 30 min 4: 95 percent / DIBALH / CH2Cl2; hexane / 0.17 h / -78 °C View Scheme

1: 95 percent / Na, liq. NH3 / tetrahydrofuran / -78 °C 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 20 min, 2.) CH2Cl2, 0 deg C, 30 min View Scheme