1: 1.) n-BuLi / 1.) ether, THF, from -78 deg C to -20 deg C, 1 h, 2.) from -78 deg C to 0 deg C 2: 95 percent / hydrazine, acetic acid / aq. ethanol / 3 h / 25 °C 3: 77 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature View Scheme

1: 93 percent / (NH4)2SO4 / toluene / Heating 2: 1.) t/BuLi; 2.) 6-bromo-1-hexene / 1.) THF-ether, -20 deg C, 1 h; 2.) THF-ether, -78 deg C View Scheme

potassium hydrogencarbonate; sodium sulfate 24 h; Yield given;

1: 1.) n-BuLi / 1) Et2O, THF, -78 --> -20 deg C, 2 h; 2) THF, Et2O, -78 deg C, 1 h, -78 deg C --> rt, overnight 2: K2CO3, Na2SO4 / CH2Cl2 / 24 h View Scheme

n-butyllithium; 5-hexenyl bromide 1.) THF-ether, -20 deg C, 1 h; 2.) THF-ether, -78 deg C; Yield given. Multistep reaction;

tert.-butyl lithium 1.) THF-ether, -20 deg C, 1 h; 2.) THF-ether, -78 deg C; Yield given. Multistep reaction;