ammonia; water in dichloromethane Product distribution / selectivity;

1: K2CO3 / ethyl acetate; H2O / 0.5 h / 3 - 8 °C 2: K2CO3 / dimethylsulfoxide / 16 h / Ambient temperature 3: 86 percent / NaBH4 / ethanol / 7 h / Ambient temperature 4: 341 g / aq. NaOH, n-Bu4NHSO4 / benzene; H2O / 0.5 h / 15 - 20 °C 5: 61 percent / NaI / tetrahydrofuran; H2O / 2.5 h / Heating 6: 21 percent / Zn / 1,2-dimethoxy-ethane / 5.5 h / Heating 7: 86 percent / H2, aq. HCl / Pd-C / tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: K2CO3 / dimethylsulfoxide / 16 h / Ambient temperature 2: 86 percent / NaBH4 / ethanol / 7 h / Ambient temperature 3: 341 g / aq. NaOH, n-Bu4NHSO4 / benzene; H2O / 0.5 h / 15 - 20 °C 4: 61 percent / NaI / tetrahydrofuran; H2O / 2.5 h / Heating 5: 21 percent / Zn / 1,2-dimethoxy-ethane / 5.5 h / Heating 6: 86 percent / H2, aq. HCl / Pd-C / tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 416 g / SOCl2 / Ambient temperature 2: K2CO3 / ethyl acetate; H2O / 0.5 h / 3 - 8 °C 3: K2CO3 / dimethylsulfoxide / 16 h / Ambient temperature 4: 86 percent / NaBH4 / ethanol / 7 h / Ambient temperature 5: 341 g / aq. NaOH, n-Bu4NHSO4 / benzene; H2O / 0.5 h / 15 - 20 °C 6: 61 percent / NaI / tetrahydrofuran; H2O / 2.5 h / Heating 7: 21 percent / Zn / 1,2-dimethoxy-ethane / 5.5 h / Heating 8: 86 percent / H2, aq. HCl / Pd-C / tetrahydrofuran / 3 h / Ambient temperature View Scheme

1: 61 percent / NaI / tetrahydrofuran; H2O / 2.5 h / Heating 2: 21 percent / Zn / 1,2-dimethoxy-ethane / 5.5 h / Heating 3: 86 percent / H2, aq. HCl / Pd-C / tetrahydrofuran / 3 h / Ambient temperature View Scheme