water

1: H2O 2: LiAlH4 3: benzene; SOCl2 View Scheme

1: H2O 2: LiAlH4 View Scheme

1: 85 percent / Et3N / CH2Cl2 / 24 h / Ambient temperature 2: 94 percent / n-BuLi / tetrahydrofuran / 1.) -25 deg C; 2.) -5 deg C to -10 deg C, 10 h 3: 70 percent / 1.) n-BuLi / tetrahydrofuran / 1.) - 25 deg C, 15 min; 2.) -78 deg C, 12 h 4: 1.) MeI, BaO; 2.) NaBH4; 3.) HCl / 1.) EtNO2, 130 deg C, 6 h; 2.) EtOH, 0 deg C to 5 deg C, 30 min; 3.) water, 0 deg C to 5 deg C, 30 min 5: 69 percent / PdCl2, CuCl, O2 / dimethylformamide; H2O / 24 h / 45 °C 6: 88 percent / KOH / H2O; dioxane / 18 h / 100 °C 7: 74 percent / Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / -78 °C View Scheme

1: H2O 2: LiAlH4 4: acetone; NaI View Scheme

ammonia in ethanol 1) -50 deg C, 2) 0 deg C, 2 h;

1: 1,2-dimethoxy-ethane / Ambient temperature 2: 1) CH3SO3H, 2) 25percent NaOH / 1) acetic acid, rt, 2) TFA, 48percent H2SO4 View Scheme

1: 85 percent / CH2Cl2 / 18 h / Ambient temperature 2: 98 percent / conc. HCl, H2 / 10percent Pd/C / ethanol / 13 h / 2585.7 Torr View Scheme