1: 50 percent / NaOH / ethanol / 2 h / Heating 2: 79 percent / KHCO3 / ethanol; H2O / 48 h 3: 40 percent / aq. NaPH / tetrahydrofuran / 2 h / Heating View Scheme

hydrazine hydrate in ethanol 5 h; Ambient temperature;

1: 1.) NaOH / 1.) EtOH, room temperature, 48 h, 2.) CHCl3, reflux, 4 h 2: EtONa / ethanol / 1.) -10 deg C, 1 h, 2.) -10 deg C -> room temperature, 24 h 3: 38 percent / NaH, CH2O gas / tetrahydrofuran / 0.08 h / -10 °C View Scheme