n-butyllithium T=-78°C;

1: 74 percent / H2NOSO3H; aq. KOH / 0 - 20 °C 2: 80 percent / (COCl)2 / CH2Cl2 / 0 - 20 °C 3: 79 percent / n-BuLi / -78 °C View Scheme

1: 80 percent / (COCl)2 / CH2Cl2 / 0 - 20 °C 2: 79 percent / n-BuLi / -78 °C View Scheme

1: 58 percent / aq. Na2Cr2O7, H2SO4 / diethyl ether / Ambient temperature 2: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 °C 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) from -78 deg C to 0 deg C, b) 0 deg C, 2 h View Scheme

1: 58 percent / 1N aq. H2SO4, Zn / Ambient temperature 2: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 °C 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) from -78 deg C to 0 deg C, b) 0 deg C, 2 h View Scheme

1: 61 percent / LiAlH4 / diethyl ether / 240 h / Heating 2: 58 percent / aq. Na2Cr2O7, H2SO4 / diethyl ether / Ambient temperature 3: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 °C 4: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) from -78 deg C to 0 deg C, b) 0 deg C, 2 h View Scheme

sodium hexamethyldisilazane T=-78°C;

1: NaHMDS / -78 °C 2: 92 percent / aq. LiOH; H2O2 / 0 - 20 °C View Scheme