methanol; potassium carbonate T=20°C; 0.5 h;

1.1: water / 70 °C 1.2: sodium azide; acetic acid / H2O; CH2Cl2 / 0 - 20 °C 2.1: imidazole / dimethylformamide / 20 °C 2.2: 158 g / sodium methoxide; methanol / 3 h / 0 °C 3.1: 95 percent / potassium carbonate; methanol / 0.5 h / 20 °C View Scheme

1: imidazole / CH2Cl2 / 1.) 0 deg C, 0.5 h, 2.) room temperature, 24 h. 2: 23.9 g / NaOMe / methanol / 6 h / Ambient temperature View Scheme