methanol; sodium methylate T=20°C; 1 h;

1: 33 percent / tetrabutylammonium hydrogen sulfate; aq. NaOH / CH2Cl2 / 3 h / 20 °C 2: 72 percent / NaOMe; MeOH / 1 h / 20 °C View Scheme

1: 33 percent / tetrabutylammonium hydrogen sulfate; aq. NaOH / CH2Cl2 / 3 h / 20 °C 2: 72 percent / NaOMe; MeOH / 1 h / 20 °C View Scheme

1: 20 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 2: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h 3: 64 percent / 0.5N sodium methoxide / methanol / 0.33 h / Ambient temperature View Scheme

1: 10 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 2: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h 3: 64 percent / 0.5N sodium methoxide / methanol / 0.33 h / Ambient temperature View Scheme

1: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h 2: 64 percent / 0.5N sodium methoxide / methanol / 0.33 h / Ambient temperature View Scheme

1: 1.) azidonitration; 2.) oxalyl chloride / 2.) CH2Cl2, DMF, 1h, 0 deg C 2: 10 percent / silver trifluoromethanesulfonate, sym-collidine, 4 Angstroem molecular sieves / CH2Cl2 / Ambient temperature 3: 1.) H2 / 1.) 5percent palladium-on-charcoal / 1.) aq. EtOH, 3h, room temperature; 2.) methanol, 6h 4: 64 percent / 0.5N sodium methoxide / methanol / 0.33 h / Ambient temperature View Scheme