pyridine; thionyl chloride 1 h; Heating;

in ethanol; water T=20°C; 0.166667 h; Green chemistry;

perchloric acid on silica gel in neat (no solvent) T=20°C; 0.25 h; Sonication;

lithium hydroxide in tetrahydrofuran T=25°C;

triethylamine in ethanol; water T=20°C; 0.666667 h;

1: 97 percent / conc. H2SO4, NBS / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) -78 deg C, 5 h 2: 94 percent / NaH / dimethylformamide / 1.) 25 deg C, 30 min, 2.) 25 deg C, 2 h 3: 1.) n-BuLi, 2.) H2 / 2.) 10percent Pd-C 4: 91 percent / DMAP / dioxane / 1 h / 100 °C 5: 76 percent / NaBH4 / ethanol / 0.5 h / 25 °C 6: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C 7: 90 percent / 9-BBN-OTf / CH2Cl2 / 0.25 h / -78 °C 8: LiOH / methanol / 0.17 h / 25 °C 9: 94 percent / aq. LiOH / tetrahydrofuran / 25 °C View Scheme

1: 76 percent / NaBH4 / ethanol / 0.5 h / 25 °C 2: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C 3: 90 percent / 9-BBN-OTf / CH2Cl2 / 0.25 h / -78 °C 4: LiOH / methanol / 0.17 h / 25 °C 5: 94 percent / aq. LiOH / tetrahydrofuran / 25 °C View Scheme

1: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C 2: 90 percent / 9-BBN-OTf / CH2Cl2 / 0.25 h / -78 °C 3: LiOH / methanol / 0.17 h / 25 °C 4: 94 percent / aq. LiOH / tetrahydrofuran / 25 °C View Scheme

1: 83 percent / Dibal-H / CH2Cl2; toluene / 1.) -78 deg C, 1.5 h, 2.) 0 deg C, 1 h 2: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C 3: 90 percent / 9-BBN-OTf / CH2Cl2 / 0.25 h / -78 °C 4: LiOH / methanol / 0.17 h / 25 °C 5: 94 percent / aq. LiOH / tetrahydrofuran / 25 °C View Scheme

1: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 16 h / 25 °C 2: 83 percent / Dibal-H / CH2Cl2; toluene / 1.) -78 deg C, 1.5 h, 2.) 0 deg C, 1 h 3: 43 percent / imidazole / dimethylformamide / 1 h / 100 °C 4: 90 percent / 9-BBN-OTf / CH2Cl2 / 0.25 h / -78 °C 5: LiOH / methanol / 0.17 h / 25 °C 6: 94 percent / aq. LiOH / tetrahydrofuran / 25 °C View Scheme