sulfuric acid 15 h; Heating;

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 89 percent / CH3ONa / methanol / 1 h View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 78 percent / CH3ONa / methanol / 1 h 7: 97 percent View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 91 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 3: 52 percent / PBr3 / CH2Cl2 / 1) 5 deg C, 1 h; 2) 3 h, room temp. 4: 42 percent / water / ethanol / 0.33 h / Heating View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 89 percent / CH3ONa / methanol / 1 h 8: 2 N HCl / 1 h View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 78 percent / CH3ONa / methanol / 1 h 7: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 78 percent / CH3ONa / methanol / 1 h 7: 2 N HCl View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 58 percent / 1) benzene, 3 h, reflux; 2) ethanol, 1 h 7: 69 percent / CH3ONa / methanol / 1 h 8: 1) HCl (g); 2) NH3 (g) / 1) chloroform, ethanol, 7 d; 2) ether, ethanol, 7 d View Scheme