Swern oxidation;

暂无反应条件数据

1: 1.) NaN(SiMe3)2 / 1.) THF, toluene, RT, 1 h, 2.) from -100 to 0 deg C, 4 h 2: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 3: 1.) NaN(SiMe3)2 / 1.) THF, HMPA, RT, 2 h, 2.) from -100 to 0 deg C, 4 h View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, -78 deg C, 20 min 2: 27 percent / Et3N, DMAP / Ambient temperature 3: 97 percent / K2CO3 / methanol; H2O / 2 h / 25 °C 4: 99 percent / imidazole / dimethylformamide / 3 h / 35 °C 5: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) benzene, 40 deg C, 2.) hexane, 5 min 6: 95 percent / <(Ph3P)4Pd>, n-BuNH2, CuI / benzene / 0.5 h 7: 85 percent / AgNO3, KCN / aq. ethanol / 0.5 h / 30 °C 8: 1.) Cp2Zr(Cl)H, 2.) I2 / 1.) THF, 35 deg C, 15 min 9: 78 percent / n-butylamine, copper iodide / Pd<P(Ph3)>4 / benzene / 3 h / Ambient temperature 10: Bu4NF / tetrahydrofuran / 2 h / Ambient temperature 11: 85 percent 12: 65 percent / Zn, MeOH / H2O / 5 h / 30 °C 13: 95 percent / K2CO3 / methanol; H2O / Ambient temperature View Scheme

1: LiAlH4 / tetrahydrofuran / 2.5 h / -90 to -20 deg C 2: 90 percent / PPh3Br2, pyridine / acetonitrile / 1 h / -7 to RT 3: 100 percent / acetonitrile / 48 h / Heating 4: 86 percent / NaN(SiMe3)2 / tetrahydrofuran / 12 h / -100 deg C to RT 5: 93 percent / DIBAH / CH2Cl2 / 1 h / -90 °C 6: 81 percent / EtAlCl2 / diethyl ether; hexane / 2.5 h / -40 to -20 deg C 7: 77 percent / 40percent aq. HF / acetonitrile / 12 h / 0 deg C to RT 8: 70 percent / Bu4NF / tetrahydrofuran / 0.25 h / -90 °C 9: 50 percent / PPh3, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 deg C to RT View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 2.5 h; -90 to -20 deg C; Yield given;

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

in tetrahydrofuran T=-78°C; 1 h;

1: 85 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C 2: 81 percent / TBAF / tetrahydrofuran 3: 92 percent / CBr4; DIPHOS 4: 96 percent / acetonitrile 5: 70 percent / LiHDMS / tetrahydrofuran / -78 - 20 °C View Scheme

1: diethyl ether / -30 - 20 °C 2: 79 percent / Na<AlH2(OCH2CH2OCH3)2> / toluene; diethyl ether / Heating View Scheme