sodium methylate in methanol

methanol; sodium methylate in dichloromethane 5 h; Ambient temperature;

methanol; sodium methylate in dichloromethane 5 h; Ambient temperature;

1: 1.) dibutyltin oxide / 1.) MeOH, reflux, 2 h, 2.) CH2Cl2, 0 deg C, 30 min 2: 91 percent / pyridine / CH2Cl2 / 5 h / 0 °C 3: 90 percent / thiourea / methanol / 2 h / Heating 4: 80 percent / 4A molecular sieves, N-iodosuccinimide, silver triflate / CH2Cl2; toluene / 0.17 h / 0 °C 5: 83 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 65 percent / K2CO3 / acetone / Ambient temperature 2: 82 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 80 percent / 4A molecular sieves, N-iodosuccinimide, silver triflate / CH2Cl2; toluene / 0.17 h / 0 °C 2: 83 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 92 percent / NaOMe, MeOH / 5 h / Ambient temperature 2: 1.) dibutyltin oxide / 1.) MeOH, reflux, 2 h, 2.) CH2Cl2, 0 deg C, 30 min 3: 91 percent / pyridine / CH2Cl2 / 5 h / 0 °C 4: 90 percent / thiourea / methanol / 2 h / Heating 5: 80 percent / 4A molecular sieves, N-iodosuccinimide, silver triflate / CH2Cl2; toluene / 0.17 h / 0 °C 6: 83 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 51 percent / pyridine / 5 h / Ambient temperature 2: 86 percent / HBr, AcOH / 1,2-dichloro-ethane / 0.5 h / Ambient temperature 3: 65 percent / K2CO3 / acetone / Ambient temperature 4: 82 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 91 percent / pyridine / CH2Cl2 / 5 h / 0 °C 2: 90 percent / thiourea / methanol / 2 h / Heating 3: 80 percent / 4A molecular sieves, N-iodosuccinimide, silver triflate / CH2Cl2; toluene / 0.17 h / 0 °C 4: 83 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 80 percent / 4A molecular sieves, N-iodosuccinimide, silver triflate / CH2Cl2; toluene / 0.17 h / 0 °C 2: 83 percent / NaOMe, MeOH / CH2Cl2 / 5 h / Ambient temperature View Scheme