sulfuric acid in methanol; water 3 h; Heating;

1: 1) n-BuLi / 1) hexane, THF, -15 deg C, 1 h, 2) HMPA, a) -15 deg C, 1 h, b) room temp., 17 h 2: p-TsOH * H2O / methanol / 18 h / Ambient temperature View Scheme

1: 1) n-BuLi / 1) hexane, THF, -15 deg C, 1 h, 2) HMPA, a) -15 deg C, 1 h, b) room temp., 17 h 2: p-TsOH * H2O / methanol / 18 h / Ambient temperature View Scheme

lithium amide 1.) ammonia, 2.) THF; Yield given. Multistep reaction;

1: 70 percent / PCC / CH2Cl2 2: 1.) NaH / 1.) THF, RT, 1 h, 2a.) 0 deg C, 1 h, 2b.) RT, 4 h 3: K, naphthalene, hexamethyldisilazane / tetrahydrofuran / 4 h / -78 °C 4: LiAlH4 / diethyl ether View Scheme

1: 70 percent / PCC / CH2Cl2 2: 1.) NaH / 1.) THF, RT, 1 h, 2a.) 0 deg C, 1 h, 2b.) RT, 4 h 3: K, naphthalene, hexamethyldisilazane / tetrahydrofuran / 4 h / -78 °C 4: LiAlH4 / diethyl ether 5: 81 percent / PPh3Br2, pyridine / CH2Cl2 / 4 h View Scheme