diisobutylaluminium hydride in toluene T=-78°C; 1 h;

1: 91 percent / sodium hypophosphite / Raney Ni / pyridine; acetic acid; H2O / 2 h / 45 - 50 °C 2: 1) water, AcOH, 0 deg C, 2) RT, 3-4 h 3: 45 percent / propan-2-ol; H2O / Ambient temperature 4: 65 percent / tetrahydrofuran / 0.5 h / 0 °C 5: diisobuthylaluminium hydride / toluene / 1 h / -78 °C View Scheme

1: 1) water, AcOH, 0 deg C, 2) RT, 3-4 h 2: 45 percent / propan-2-ol; H2O / Ambient temperature 3: 65 percent / tetrahydrofuran / 0.5 h / 0 °C 4: diisobuthylaluminium hydride / toluene / 1 h / -78 °C View Scheme

1: 65 percent / tetrahydrofuran / 0.5 h / 0 °C 2: diisobuthylaluminium hydride / toluene / 1 h / -78 °C View Scheme

1: 45 percent / propan-2-ol; H2O / Ambient temperature 2: 65 percent / tetrahydrofuran / 0.5 h / 0 °C 3: diisobuthylaluminium hydride / toluene / 1 h / -78 °C View Scheme