Multistep reaction;

Multistep reaction;

hydrogenchloride 4 h; Ambient temperature;

1: 100 percent / N-bromosuccinimide, 2,2-azadiisobutyronitrile / CCl4 / 5 h / Heating 2: 62 percent / H2O / dioxane / 2.5 h / Heating 3: 72 percent / conc. HCl / 4 h / Ambient temperature View Scheme

1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min 2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C 6: diethyl ether / 1 h View Scheme

1: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 2: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 3: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 4: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating 5: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating 6: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature 7: 1.86 g / NaOH / methanol; H2O / 2 h / Heating 8: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C 9: 0.96 g / diethyl ether View Scheme

1: 1.) H2SO4, H2O2 (28percent w/v), 2.) NaOH / 1.) 40 deg C, 8 h, 2.) MeOH, water, reflux, 5 h 2: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 3: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 4: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 5: 40 g / 10percent aq. NaOH / 4 h / Heating 6: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 7: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 8: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 9: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 10: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating 11: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating 12: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature 13: 1.86 g / NaOH / methanol; H2O / 2 h / Heating 14: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C 15: 0.96 g / diethyl ether View Scheme

1: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 2: 40 g / 10percent aq. NaOH / 4 h / Heating 3: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 4: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 5: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 6: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 7: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating 8: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating 9: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature 10: 1.86 g / NaOH / methanol; H2O / 2 h / Heating 11: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C 12: 0.96 g / diethyl ether View Scheme

1: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 2: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 3: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 4: 40 g / 10percent aq. NaOH / 4 h / Heating 5: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 6: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 7: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 8: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 9: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating 10: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating 11: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature 12: 1.86 g / NaOH / methanol; H2O / 2 h / Heating 13: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C 14: 0.96 g / diethyl ether View Scheme

1: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 2: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 3: 40 g / 10percent aq. NaOH / 4 h / Heating 4: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 5: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 6: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 7: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 8: 35 percent / t-butyl chromate / CCl4 / 24 h / Heating 9: 3.25 g / aluminium isopropoxide / propan-2-ol / 6 h / Heating 10: 3.2 g / POCl3 / benzene / 2.5 h / Ambient temperature 11: 1.86 g / NaOH / methanol; H2O / 2 h / Heating 12: 1.6 g / Jones' reagent / acetone / 0.17 h / -10 °C 13: 0.96 g / diethyl ether View Scheme