lithium borohydride in tetrahydrofuran T=20°C;

1: triethylamine / ethyl acetate; N,N-dimethyl-formamide / 4 h / 30 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 5 h / -5 °C View Scheme

in N,N-dimethyl-formamide 5 h; Cooling with iceAlkaline conditions;

1: With sodium hydrogencarbonate in N,N-dimethyl acetamide T=40°C; 3 - 4 h; 2: With sodium acetate in water T=20°C; 4 h;

potassium carbonate in N,N-dimethyl acetamide T=30°C; 6 h;

1: 1.) O3, 2.) dimethyl sulfide, 3.) p-toluenesulfonic acid, 4.) camphorsulfonic acid / 1) MeOH, -78 deg C, 10 min; 2) MeOH, 0-20 deg C, 3 h; 3) benzene, 25 deg C, 17 h; 4) 1,2-dichloroethane, reflux, 48 h 2: 83 percent / thioanisole, 2,2,2,-trifluoroacetic acid / CH2Cl2 / 6 h / 25 °C View Scheme

1: 1.) O3, 2.) dimethyl sulfide, 3.) p-toluenesulfonic acid, 4.) camphorsulfonic acid / 1) MeOH, -78 deg C, 10 min; 2) MeOH, 0-20 deg C, 3 h; 3) benzene, 25 deg C, 17 h; 4) 1,2-dichloroethane, reflux, 48 h 2: 83 percent / thioanisole, 2,2,2,-trifluoroacetic acid / CH2Cl2 / 6 h / 25 °C View Scheme

1: 1.) Py, 2.) DMAP / 1.) MeCN, 0 deg C, 15 min, 2.) 23 deg C, 30 min 2: 88 percent / HCl(gas), HCOOH / toluene / 19 h 3: KOH / H2O; methanol; tetrahydrofuran / 10 h / 100 °C 4: tetrahydrofuran View Scheme

1: 99 percent / DCC, Cl2CHCOOH / dimethylsulfoxide / 0.25 h / 23 °C 2: 1.) Py, 2.) DMAP / 1.) MeCN, 0 deg C, 15 min, 2.) 23 deg C, 30 min 3: 88 percent / HCl(gas), HCOOH / toluene / 19 h 4: KOH / H2O; methanol; tetrahydrofuran / 10 h / 100 °C 5: tetrahydrofuran View Scheme

1: 93 percent / NaBH4 / ethanol; tetrahydrofuran / 23 °C 2: 98 percent / Py, DMAP / 0.17 h / 23 °C 3: m-CPBA / tetrahydrofuran / 0.17 h / 23 °C 4: Et3N, DHP / 0.5 h / 80 °C 5: 93 percent / KI, I2, DBU / tetrahydrofuran / 0.67 h / 23 °C 6: 98 percent / nBu3SnH, AIBN / acetonitrile / 0.83 h / Heating 7: 90 percent / K2CO3 / methanol / 0.17 h / 23 °C 8: 99 percent / DCC, Cl2CHCOOH / dimethylsulfoxide / 0.25 h / 23 °C 9: 1.) Py, 2.) DMAP / 1.) MeCN, 0 deg C, 15 min, 2.) 23 deg C, 30 min 10: 88 percent / HCl(gas), HCOOH / toluene / 19 h 11: KOH / H2O; methanol; tetrahydrofuran / 10 h / 100 °C 12: tetrahydrofuran View Scheme