lithium borohydride in tetrahydrofuran 20 h; Ambient temperature;

potassium carbonate; potassium iodide in butan-1-ol 16 h; Heating;

1: 78.5 percent / 7percent aqueous ammonia 2: 67 percent / LiBH4 / tetrahydrofuran / 20 h / Ambient temperature View Scheme

1: CHCl3 / Heating 2: NaHCO3 / H2O; ethanol / 70 °C 3: SOCl2 / CHCl3 / Heating 4: 62.3 percent / EtONa / ethanol / 1 h / Ambient temperature 5: 52.6 percent / KOH / ethanol; H2O / 1 h / Ambient temperature View Scheme