1: 91 percent / Ph3P, imidazole, I2 / CH2Cl2 / 1 h 2: 97 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 1h, 2.) -78 deg C, 1 h, -78 deg C to 0 deg C, 2 h 3: 80 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 2 h, 2.) -78 deg C, 1h 4: 1.) t-BuLi, 2.) n-Bu4NH2PO4 / 1.) THF, -78 deg C, 1 h, 2.) H2O, reflux, 12 h 5: NaOEt / ethanol / 24 h / Heating View Scheme

pyridine; bromine in dichloromethane T=20°C; 2 h;

lithium aluminium tetrahydride in diethyl ether T=25 - 30°C; 2 h;

diisobutylaluminium hydride in hexane; dichloromethane T=-78 - -8°C; 3 h;

1.1: methyl chloroformate; triethylamine / tetrahydrofuran / 1 h / -20 °C 1.2: 96 percent / sodium borohydride / tetrahydrofuran; H2O / 64 h / 0 - 24 °C 2.1: Br2 / CHCl3 View Scheme

1: 92 percent / ethanol; H2O / 5 h / Heating 2: 90 percent / sulfuric acid / 6 h / Heating 3: 96 percent / DIBAL-H / CH2Cl2; hexane / 3 h / -78 - -8 °C View Scheme

1: 90 percent / sulfuric acid / 6 h / Heating 2: 96 percent / DIBAL-H / CH2Cl2; hexane / 3 h / -78 - -8 °C View Scheme

1: 73 percent / lithium aluminum hydride / tetrahydrofuran / 22 h / 25 °C 2: 88 percent / bromine, pyridine / CH2Cl2 / 16 h / 25 °C View Scheme

1: conc. H2SO4 / 7 h / Heating 2: 93 percent / LiAlH4 / diethyl ether / 2 h / 25 - 30 °C View Scheme

1: 69 percent / Br2, (PhCO2)2 / CCl4 / 1 h / Heating 2: dimethylsulfoxide / 0.75 h / Ambient temperature 3: aq. KOH / ethanol / 14 h / Heating 4: conc. H2SO4 / 7 h / Heating 5: 93 percent / LiAlH4 / diethyl ether / 2 h / 25 - 30 °C View Scheme