diisobutylaluminium hydride in hexane; toluene T=-78°C; 4 h;

1: 11.5 g / tetrahydrofuran / 1 h / -78 °C 2: 4.5 percent / Zn-Ag / methanol; diethyl ether / 18 h 3: 94 percent / diisobutylaluminum hydride / hexane; toluene / 4 h / -78 °C View Scheme

1: SOCl2 / benzene / 3 h / Heating 2: 11.5 g / tetrahydrofuran / 1 h / -78 °C 3: 4.5 percent / Zn-Ag / methanol; diethyl ether / 18 h 4: 94 percent / diisobutylaluminum hydride / hexane; toluene / 4 h / -78 °C View Scheme

1: 4.5 percent / Zn-Ag / methanol; diethyl ether / 18 h 2: 94 percent / diisobutylaluminum hydride / hexane; toluene / 4 h / -78 °C View Scheme

1: 11.5 g / tetrahydrofuran / 1 h / -78 °C 2: 4.5 percent / Zn-Ag / methanol; diethyl ether / 18 h 3: 94 percent / diisobutylaluminum hydride / hexane; toluene / 4 h / -78 °C View Scheme