trifluoroacetic acid in tetrahydrofuran; water 3 h; Ambient temperature;

lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C; 3 h;

1.1: aq. NaOH; cetyltrimethylammonium chloride / 1,2-dichloro-ethane / 5 h / 80 °C 2.1: 48 mg / p-TsOH / 12 h / 80 °C 3.1: 86 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.33 h / -78 °C 4.1: n-BuLi / diethyl ether; hexane / 0.08 h / 0 °C 4.2: 62 percent / diethyl ether; hexane / 0.17 h / 0 °C 5.1: 83 percent / H2 / Pd/C / ethanol / 2.5 h 6.1: 89 percent / HCl / methanol / 7 h / 20 °C 7.1: 77 percent / K2CO3 / methanol / 0.33 h / 20 °C 8.1: 84 percent / NaBH4 / methanol / 0.5 h / 20 °C View Scheme

lithium aluminium tetrahydride; sodium sulfate in tetrahydrofuran