sodium methylate; silver trifluoromethanesulfonate; N,N,N',N'-tetramethyl-urea 1.) CH2Cl2, 20 deg C, 16 h; 2.) MeOH, 20 deg C, 16 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 39.8 percent / AgSO3CF3, Me2NCONMe2 / CH2Cl2 / 1.) -10 to 20 deg C, 3 h; 2.) 20 deg C, 4 d 2: 82.2 percent / AgSO3CF3, Me2NCONMe2 / CH2Cl2 / 1.) -10 to 20 deg C, 3.5 h; 2.) 20 deg C, 16 h 3: 87.2 percent / NaOMe / methanol; tetrahydrofuran / 16 h / 20 °C 4: 24 mg / H2 / Pd-C (10percent) / ethanol; H2O / 4.5 h / 50 °C View Scheme

1: 1.) AgSO3CF3, Me2NCONMe2; 2.) NaOMe / 1.) CH2Cl2, 20 deg C, 16 h; 2.) MeOH, 20 deg C, 16 h 2: pyridine View Scheme