carbonic acid diphenyl ester; sodium hydrogencarbonate in N,N-dimethyl-formamide T=144 - 145°C; 0.416667 h;

sodium hydroxide in methanol 6 h;

1: 70percent aq. acetic acid / 16 h / Ambient temperature 2: 85.8 percent / pyridine / 96 h / Ambient temperature 3: 83 percent / NaI / butan-2-one / 18 h / Heating 4: 1.)I2, silver trifluoroacetate 2.) H2, W-4 Raney nickel, triethylamine / 1.)DME, r.t., 15 min; 2.) MeOH, 3 h, 0.3-0.35 MPa 5: 91 percent / NaOMe / methanol / 10 h / 5 - 20 °C / Irradiation 6: 89 percent / pyridine 7: 83 percent / acetolysis 8: 62 percent / tin(IV) chloride 9: 84 percent / deacylation 10: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme

1: 78 percent / conc. H2SO4 / acetic acid / 72 h / Ambient temperature 2: 46 percent / tin(IV) chloride / 1,2-dichloro-ethane / Ambient temperature 3: 97 percent / 1M aq. NaOH / methanol / 6 h View Scheme

1: 83 percent / acetolysis 2: 62 percent / tin(IV) chloride 3: 84 percent / deacylation 4: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme

1: 62 percent / tin(IV) chloride 2: 84 percent / deacylation 3: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme

1: 89 percent / pyridine 2: 83 percent / acetolysis 3: 62 percent / tin(IV) chloride 4: 84 percent / deacylation 5: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme

1: 1.)I2, silver trifluoroacetate 2.) H2, W-4 Raney nickel, triethylamine / 1.)DME, r.t., 15 min; 2.) MeOH, 3 h, 0.3-0.35 MPa 2: 91 percent / NaOMe / methanol / 10 h / 5 - 20 °C / Irradiation 3: 89 percent / pyridine 4: 83 percent / acetolysis 5: 62 percent / tin(IV) chloride 6: 84 percent / deacylation 7: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme

1: 46 percent / tin(IV) chloride / 1,2-dichloro-ethane / Ambient temperature 2: 97 percent / 1M aq. NaOH / methanol / 6 h View Scheme

1: 83 percent / NaI / butan-2-one / 18 h / Heating 2: 1.)I2, silver trifluoroacetate 2.) H2, W-4 Raney nickel, triethylamine / 1.)DME, r.t., 15 min; 2.) MeOH, 3 h, 0.3-0.35 MPa 3: 91 percent / NaOMe / methanol / 10 h / 5 - 20 °C / Irradiation 4: 89 percent / pyridine 5: 83 percent / acetolysis 6: 62 percent / tin(IV) chloride 7: 84 percent / deacylation 8: 49 percent / diphenylcarbonate, NaHCO3 / dimethylformamide / 0.42 h / 144 - 145 °C View Scheme