sulfuric acid; acetic anhydride

sulfuric acid T=50°C; 1 h;

tin(IV) chloride T=130°C;

tin(IV) chloride T=130°C;

1: 97 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: 76 percent / aq. KOH / ethanol / 3 h / Heating 5: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 6: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 90 percent / K2CO3 / acetone / 3 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: 97 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: 76 percent / aq. KOH / ethanol / 3 h / Heating 5: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 6: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 60 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: 68 percent / conc. HCl / ethanol / 1 h / Heating View Scheme

1: 97 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: 76 percent / aq. KOH / ethanol / 3 h / Heating 5: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 6: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 60 percent / K2CO3 / acetone; dimethylformamide / 18 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: 97 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: 76 percent / aq. KOH / ethanol / 3 h / Heating 5: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 6: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 90 percent / K2CO3 / acetone / 3 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating View Scheme

1: 97 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 4 h / Heating 2: thionyl chloride / toluene / 1 h / 80 °C 3: ethanol; H2O / 12 h / Heating 4: 76 percent / aq. KOH / ethanol / 3 h / Heating 5: 83 percent / polyphosphoric acid / toluene / 4 h / Heating 6: 95 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / CH2Cl2 / 0.5 h 7: 58 percent / pyridine hydrochloride / 0.5 h / 210 °C 8: 90 percent / K2CO3 / acetone / 3 h / Heating 9: 1.) BuLi / 1.) THF, -70 deg C, 1 h, 2.) THF, RT, 18 h 10: conc. HCl / ethanol / 1 h / Heating 11: 1.) OsO4, 2.) H2S / 1.) THF, RT, 18 h View Scheme

sulfuric acid T=50°C; 1 h;