sodium methylate in 1,4-dioxane; methanol 0.25 h; Ambient temperature;

Dowex 50 resin in tetrahydrofuran; methanol 0.5 h;

1: 48.3 percent / triphenylphosphine, diethyl azodicarboxylate / dioxane / 48 h / 24 °C 2: 93 percent / NaOH / methanol / 48 h / Ambient temperature 3: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H2O / 30 h / 37 - 40 °C / pH=4.5 4: 89 percent / pyridine / 12 h 5: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C 6: 65 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 3 h / Heating View Scheme

1: 48.3 percent / triphenylphosphine, diethyl azodicarboxylate / dioxane / 48 h / 24 °C 2: 93 percent / NaOH / methanol / 48 h / Ambient temperature 3: 47.9 percent / aq. sodium acetate, aq. acetic acid, KI / ethanol; H2O / 30 h / 37 - 40 °C / pH=4.5 4: 89 percent / pyridine / 12 h 5: 50 percent / 4-(dimethylamino)pyridine / acetonitrile / 12 h / 24 °C View Scheme