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

1.1: potassium hydroxide / dimethyl sulfoxide / 2 h / 0 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 2.2: 20 °C 3.1: toluene / 5 h / 20 °C 4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C View Scheme

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C 1.2: 20 °C 2.1: toluene / 5 h / 20 °C 3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C View Scheme

1: toluene / 5 h / 20 °C 2: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C View Scheme