1: 93 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 2: 70 percent / pyridine / 3 h / Heating 3: 86 percent / liq. NH3 / diethyl ether / 12 h / Ambient temperature 4: 91 percent / Ag2O / diethyl ether / 1 h 5: 92 percent / conc. HCl / methanol 6: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature 7: 73 percent / N,N'-dicyclohexylcarbodiimide / dioxane; ethyl acetate / 6 h / Ambient temperature View Scheme

1.1: 60 percent / hydroxylamine hydrochloride / ethanol / 60 °C 2.1: 65 percent / N,N-DMAP; triethylamine / CH2Cl2 / 0 - 20 °C 3.1: NH3 / diethyl ether / -60 °C 3.2: 55 percent / triethylamine; I2 / methanol / 0 - 20 °C 4.1: 77 percent / HCl / methanol / 20 °C View Scheme

1: 93 percent / NH3OHCl, NaOH / ethanol / 16 h / Heating 2: 70 percent / pyridine / 3 h / Heating 3: 86 percent / liq. NH3 / diethyl ether / 12 h / Ambient temperature 4: 91 percent / Ag2O / diethyl ether / 1 h 5: 92 percent / conc. HCl / methanol 6: 72 percent / 0.2N KOH, KMnO4 / dioxane / 2 h / Ambient temperature View Scheme

n-butyllithium in tetrahydrofuran; hexane T=-74°C; 1.25 h;

1: (4-bromo-benzyloxy)-tert-butyl-dimethyl-silane With n-butyllithium in tetrahydrofuran T=-30°C; 2: N-(trifluoroacetyl)piperidine in tetrahydrofuran T=-50°C;

1: 4-(tert-butyldimethylsiloxymethyl)iodobenzene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.75 h; 2: ethyl-α,α,α-trifluoroacetate in tetrahydrofuran; hexane T=-78°C; 1.25 h;

1.1: 87 percent / imidazole / dimethylformamide / 20 °C 2.1: nBuLi / tetrahydrofuran / -30 °C 2.2: 89 percent / tetrahydrofuran / -50 °C View Scheme

1.1: 87 percent / imidazole / dimethylformamide / 20 °C 2.1: nBuLi / tetrahydrofuran / -30 °C 2.2: 89 percent / tetrahydrofuran / -50 °C View Scheme

n-butyllithium in diethyl ether T=-78°C;

1.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: 1.25 h / -78 °C View Scheme