lithium aluminium tetrahydride in tetrahydrofuran

oxalic acid T=150°C; P=4484 Torr; 2.5 h;

1: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 3: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 4: 1) Mg / 1) ether, 2) 0 deg C, 15 min 5: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 2: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 3: 1) Mg / 1) ether, 2) 0 deg C, 15 min 4: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 2: 1) Mg / 1) ether, 2) 0 deg C, 15 min 3: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1: 1) Mg / 1) ether, 2) 0 deg C, 15 min 2: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1: 92 percent / BF3*Et2O / CH2Cl2 / 6 h / Ambient temperature 2: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 3: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 4: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 5: 1) Mg / 1) ether, 2) 0 deg C, 15 min 6: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

(i) O3, CH2Cl2, (ii) LiAlH4, THF; Multistep reaction;

1: 91 percent / SOCl2 / 0 °C 2: 88 percent / BF3*THF / 18 h / Heating View Scheme

lithium aluminium tetrahydride; ozone 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; different ozonolysis temperature; Product distribution;