n-butyllithium in tetrahydrofuran T=-78 - 20°C; 4 h;

1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; Inert atmosphere; 2: With formaldehyd in tetrahydrofuran; hexane T=-78 - 20°C; 4 h; Inert atmosphere;

1: 99 percent / imidazole / CH2Cl2 2: 99 percent / n-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C View Scheme

1: 97 percent / KOH / diethyl ether / 1 h / 0 °C 2: 87 percent / K2CO3, NaI, CuI / dimethylformamide / 28 h / Ambient temperature 3: 73 percent / TBAF / tetrahydrofuran / 1.1 h / -20 °C View Scheme

1: H2 / Lindlar catalyst / benzene / Ambient temperature 2: 74 percent / (D)-(-)-DIPT, Ti(OiPr)4, TBHP, 4A MS / CH2Cl2 / 64 h / -30 °C View Scheme

1: KOH / diethyl ether 3: 8.3 g / p-toluenesulfonic acid / methanol / 2 h / 20 °C 4: CrO3 - 1,5M H2SO4 / acetone / 1.)0 deg C, 2.)20 deg C, 2 h 5: 64 percent / H2O, conc. HCl / tetrahydrofuran / 24 h / 20 °C 6: H2 / P-2 nickel / ethanol 7: 27 percent / Triethylamine, 2-Chloro-1-methylpyridinium iodide / acetonitrile / Heating View Scheme

sodium bis(2-methoxyethoxy)aluminium dihydride in diethyl ether; toluene T=20°C; 16 h;