sodium methylate in ethanol Heating;

1: 84 percent / conc. H2SO4 / 1.5 h / 120 °C 2: 71 percent / POCl3 / 2 h / Heating 3: 87 percent / methanol / 48 h / Heating 4: 1) n-BuLi / 1) THF, hexane, -78 deg C, 5 min, 2) to -20 deg C 5: 46 percent / NaOMe / dimethylsulfoxide / 2 h / 90 - 95 °C 6: 14 percent / NaOMe / ethanol / Heating View Scheme

1: 71 percent / POCl3 / 2 h / Heating 2: 87 percent / methanol / 48 h / Heating 3: 1) n-BuLi / 1) THF, hexane, -78 deg C, 5 min, 2) to -20 deg C 4: 46 percent / NaOMe / dimethylsulfoxide / 2 h / 90 - 95 °C 5: 14 percent / NaOMe / ethanol / Heating View Scheme

1: 87 percent / methanol / 48 h / Heating 2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 5 min, 2) to -20 deg C 3: 46 percent / NaOMe / dimethylsulfoxide / 2 h / 90 - 95 °C 4: 14 percent / NaOMe / ethanol / Heating View Scheme

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 5 min, 2) to -20 deg C 2: 46 percent / NaOMe / dimethylsulfoxide / 2 h / 90 - 95 °C 3: 14 percent / NaOMe / ethanol / Heating View Scheme

1: 46 percent / NaOMe / dimethylsulfoxide / 2 h / 90 - 95 °C 2: 14 percent / NaOMe / ethanol / Heating View Scheme