lithium aluminium tetrahydride in diethyl ether T=20°C;

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / 0 °C 1.2: tetrahydrofuran; hexane / 0 - 20 °C 2.1: 11.3 g / lithium aluminium hydride / diethyl ether / 0 - 20 °C View Scheme

1: 97 percent / MgSO4 / CH2Cl2 / Ambient temperature 2: 89 percent / t-BuOK / tetrahydrofuran / 1 h / Heating 3: 1.) aq. oxalic acid, 2.) aq. NaOH / 1.) CH2Cl2, reflux, 2 h, 2.) 0 deg C View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 2.5 h; Heating;

phthalimide; triphenylphosphine; hydrazine; diethylazodicarboxylate 1.) THF, 25 deg C, 3 d, 2.) MeOH, reflux, 10 h; Yield given. Multistep reaction;

1: 97 percent / MgSO4 / CH2Cl2 / 1 h / Heating 2: 1.) LDA / 1.) THF, hexane, 0 deg C, 2.) THF, hexane, 0 deg C -> room temperature, 16 h 3: 80 percent / oxalic acid dihydrate / CH2Cl2; H2O / 2 h / Heating 4: 97 percent / MgSO4 / CH2Cl2 / Ambient temperature 5: 89 percent / t-BuOK / tetrahydrofuran / 1 h / Heating 6: 1.) aq. oxalic acid, 2.) aq. NaOH / 1.) CH2Cl2, reflux, 2 h, 2.) 0 deg C View Scheme

1: 72 percent / iPr2NLi / tetrahydrofuran / 2 h / -78 °C 2: 92 percent / 15percent ethanolic KOH / 48 h / Heating 3: sodium, oxalyl chloride / diethyl ether / 3 h / Heating 4: ammonia / diethyl ether / ice-cooling 5: 83 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Heating View Scheme

1: ammonia / diethyl ether / ice-cooling 2: 83 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Heating View Scheme

1: 92 percent / 15percent ethanolic KOH / 48 h / Heating 2: sodium, oxalyl chloride / diethyl ether / 3 h / Heating 3: ammonia / diethyl ether / ice-cooling 4: 83 percent / LiAlH4 / tetrahydrofuran / 2.5 h / Heating View Scheme