1.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 3.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C 3.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C 4.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C View Scheme

1.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 2.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 3.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C 3.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C 4.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C 5.1: 99 percent / HCl / diethyl ether View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 1 h;

1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 2: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 3: 82 percent / tetrahydrofuran; H2O / 4 h / 60 - 65 °C View Scheme