1: 85 percent / NaH, Bu4NI / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temp., overnight 2: 70 percent / SOCl2, pyridine / CH2Cl2 / 5.5 h / 0 °C 3: 85 percent / CF3COOH, H2O / CH2Cl2 / 24 h / Ambient temperature 4: 95 percent / SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C 5: 90 percent / LiN3 / dimethylformamide / 3 h / 80 °C 6: 95 percent / pyridine / CH2Cl2 / 3 h / 0 °C 7: 27 percent / dimethylformamide / 80 °C 8: 100 percent / K2CO3 / methanol / 12 h / Ambient temperature 9: 97 percent / PPh3 / pyridine; aq. NH3 / Ambient temperature 10: Na / tetrahydrofuran; liquid ammonia / 4 h / -78 °C View Scheme

1: 90 percent / DMAP / triethylamine / 3 h / Heating 2: 90 percent / TFA, H2O / CH2Cl2 / 24 h / Ambient temperature 3: 93 percent / pyridine / CH2Cl2 / 1 h / 0 °C 4: 60 percent / NaN3, benzo-15-crown-5 / dimethylformamide / Ambient temperature 5: 90 percent / pyridine / CH2Cl2 / 0.17 h / 0 °C 6: 80 percent / tetrahydrofuran / 1 h / Ambient temperature 7: 91 percent / K2CO3 / methanol / 2 h / Ambient temperature 8: 80 percent / H2 / 20percent Pd(OH)2 on charcoal / ethanol View Scheme