titanium tetrachloride in dichloromethane a) 0 deg C, 30 min, b) reflux, 1 h;

1: 90 percent / H2 / 5percent Pd/C / aq. ethanol / 2 h / 2585.7 Torr 2: 83 percent / TiCl4 / CH2Cl2 / a) 0 deg C, 30 min, b) reflux, 1 h View Scheme

1: p-toluenesulfonic acid / toluene / Heating 2: 90 percent / H2 / 5percent Pd/C / aq. ethanol / 2 h / 2585.7 Torr 3: 83 percent / TiCl4 / CH2Cl2 / a) 0 deg C, 30 min, b) reflux, 1 h View Scheme

1: 1) Mg / 1) Et2O; 2) Et2O, rflux, overnight 2: p-toluenesulfonic acid / toluene / Heating 3: 90 percent / H2 / 5percent Pd/C / aq. ethanol / 2 h / 2585.7 Torr 4: 83 percent / TiCl4 / CH2Cl2 / a) 0 deg C, 30 min, b) reflux, 1 h View Scheme

ammonium acetate Heating;

1: 82 percent / CH3COONH4 / Heating 2: LiAlH4 / diethyl ether View Scheme