sodium methylate in methanol 16 h;

toluene-4-sulfonic acid in methanol; dichloromethane 0.5 h; Ambient temperature;

1: AcOH, conc. H2SO4 / CH2Cl2 / 16 h / 4 °C 2: 46 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 4 h / Heating 3: 83 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 2 h / 90 °C 4: (dimethylamino)pyridine / acetonitrile 5: 89 percent / tributyltin hydride, AIBN / toluene / 120 °C 6: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 7: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

1: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 2: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

1: (dimethylamino)pyridine / acetonitrile 2: 89 percent / tributyltin hydride, AIBN / toluene / 120 °C 3: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 4: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

1: 46 percent / hexamethyldisilazane, chlorotrimethylsilane, trifluoromethanesulfonic acid / acetonitrile / 4 h / Heating 2: 83 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 2 h / 90 °C 3: (dimethylamino)pyridine / acetonitrile 4: 89 percent / tributyltin hydride, AIBN / toluene / 120 °C 5: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 6: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

1: 89 percent / tributyltin hydride, AIBN / toluene / 120 °C 2: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 3: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

1: 83 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / toluene / 2 h / 90 °C 2: (dimethylamino)pyridine / acetonitrile 3: 89 percent / tributyltin hydride, AIBN / toluene / 120 °C 4: 50 percent / LiN3, benzoic acid / dimethylformamide / 16 h / 120 °C 5: 82 percent / 0.1 M NaOCH3 / methanol View Scheme

1: 96 percent / pyridine / 2 h / Ambient temperature 2: 67 percent / pyridine / 1.5 h / Ambient temperature 3: 50 percent / Bu3SnH, AIBN / toluene / 2 h / Heating 4: 91 percent / pyridine / 2 h / Ambient temperature 5: 74 percent / NaN3 / dimethylformamide / 2 h / Heating 6: 71 percent / TsOH / methanol; CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: TMSOTf / acetonitrile / 4 h / Ambient temperature 2: NaOMe / methanol / 1 h / Ambient temperature 3: 96 percent / pyridine / 2 h / Ambient temperature 4: 67 percent / pyridine / 1.5 h / Ambient temperature 5: 50 percent / Bu3SnH, AIBN / toluene / 2 h / Heating 6: 91 percent / pyridine / 2 h / Ambient temperature 7: 74 percent / NaN3 / dimethylformamide / 2 h / Heating 8: 71 percent / TsOH / methanol; CH2Cl2 / 0.5 h / Ambient temperature View Scheme