lithium hydroxide in tetrahydrofuran; water T=0°C; 0.5 h;

1: 93 percent / aq. NaOH / 0.1 h / ice cooling 2: 63 percent / Et3N; CuI / (Ph3P)4Pd / tetrahydrofuran / 23 h / 20 °C 3: aq. LiOH / tetrahydrofuran View Scheme

hydrogenchloride 24 h; Ambient temperature;

1: 50 percent / I2, KI, Me2NH / 3 h 2: 89 percent / P2O5 / CH2Cl2 / 5 h 3: 99 percent / Et3N / Pd(OAc)2, TPPTS / acetonitrile; H2O / 12 h / Ambient temperature 4: 38 percent / POCl3 / pyridine / 12 h / Ambient temperature 5: 99 percent / 1percent aq. HCl / 24 h / Ambient temperature View Scheme

1: 63 percent / Et3N; CuI / (Ph3P)4Pd / tetrahydrofuran / 23 h / 20 °C 2: aq. LiOH / tetrahydrofuran View Scheme

lithium hydroxide in tetrahydrofuran

1: 72 percent / Ac2O, conc. H2SO4 / 50 °C 2: 85 percent / CuI, Et2NH / <Pd(PPh3)2Cl2> / Ambient temperature 3: 78 percent / 12N HCl, HOAc / 8 h / Ambient temperature View Scheme

1: 85 percent / CuI, Et2NH / <Pd(PPh3)2Cl2> / Ambient temperature 2: 78 percent / 12N HCl, HOAc / 8 h / Ambient temperature View Scheme

1: 1) CuI, aq. NH4OH, NH2OH*HCl / 1) EtOH, 15 min, 2) DMF, 110 to 120 deg C, 3 h 2: 62 percent / 3percent aq. NaOH / ethanol / 2 h View Scheme