sodium methylate in methanol T=0°C; 30 h;

1: 89 percent / triethylamine / CH2Cl2 / 0.5 h 2: 1.) NaH / 1.) DMF, 0 deg C, 10 min, 2.) DMF, 65 deg C, 3 h 3: 76 percent / sodium methoxide / methanol / 30 h / 0 °C View Scheme

1: 1.) NaH / 1.) DMF, 0 deg C, 10 min, 2.) DMF, 65 deg C, 3 h 2: 76 percent / sodium methoxide / methanol / 30 h / 0 °C View Scheme

1: 1.) sodium methoxide, 2.) NaH / 1.) MeOH, 1 h, 2.) THF, CH2Cl2, 1 h 2: 89 percent / triethylamine / CH2Cl2 / 0.5 h 3: 1.) NaH / 1.) DMF, 0 deg C, 10 min, 2.) DMF, 65 deg C, 3 h 4: 76 percent / sodium methoxide / methanol / 30 h / 0 °C View Scheme

2: 51 percent / H2 / Pd-C View Scheme