n-butyllithium in tetrahydrofuran T=-78°C; 1 h;

in tetrahydrofuran T=-78°C; 1 h;

1: 53 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 4 h; 2.) 27 deg C, 40 h 2: 83 percent / hydrogen / Pd/BaSO4 / methanol / 30 h 3: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 4: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C View Scheme

1: 70 percent / HMPT / tetrahydrofuran / -5 °C 2: 82 percent / hydrogen / P-2 Ni / ethanol 3: trifluoroacetic acid, water / CHCl3 / 1 h 4: tetrahydrofuran / 1 h / -78 to 20 deg C View Scheme

1: 83 percent / hydrogen / Pd/BaSO4 / methanol / 30 h 2: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 3: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C View Scheme

1: 65.4 percent / pyridinium chlorochromate (PCC) / CH2Cl2 / 1 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, -78 deg C, 20 min View Scheme

1: 93 percent / oxalic acid / acetone; H2O / 1 h / 60 °C 2: 62 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C View Scheme

1: 83 percent / sodium hydride / dimethylformamide / 20 h / Ambient temperature 2: 93 percent / dimethylaminopyridine / CH2Cl2 / 20 h / Ambient temperature 3: 95 percent / 55 percent aq. hydriodic acid / benzene / 20 h / Ambient temperature 4: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 27 percent / Et3N, DMAP / Ambient temperature 2: 97 percent / K2CO3 / methanol; H2O / 2 h / 25 °C 3: 99 percent / imidazole / dimethylformamide / 3 h / 35 °C 4: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) benzene, 40 deg C, 2.) hexane, 5 min 5: 95 percent / <(Ph3P)4Pd>, n-BuNH2, CuI / benzene / 0.5 h 6: 85 percent / AgNO3, KCN / aq. ethanol / 0.5 h / 30 °C 7: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) THF, 35 deg C, 15 min 8: 78 percent / n-butylamine, copper iodide / Pd<P(Ph3)>4 / benzene / 3 h / Ambient temperature 9: Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 10: 85 percent 11: 65 percent / Zn, MeOH / H2O / 5 h / 30 °C 12: 95 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: 97 percent / Jones reagent / diethyl ether / 2 h / 25 °C 2: 1.) n-butyllithium, 2.) cuprous bromide dimethylsulfide complex / 1.) THF, -78 deg C, 1.5 h; 2.) ether, -50 deg C, 1 h, 3.) -50 deg C, 1 min, glacial acetic acid in methanol 3: 92 percent / NaBH4 / methanol / 0.25 h / -40 °C 4: 1.) NaHSO4; 2.) LiOH / 1.) dimethoxy ethane-water, O deg C, 3 min; 2.) 25 deg C, 1 hr View Scheme