magnesium; copper(I) bromide 1.) THF, 30 deg C, 30 min, 2.) THF, 20 deg C, 1 h; Yield given. Multistep reaction;

1.1: 54 percent / DCC; Et3N / CH2Cl2 / 0 - 20 °C 2.1: Mg / tetrahydrofuran / 1 h / 20 °C 2.2: Amberlite IRC-50 / tetrahydrofuran View Scheme

in tetrahydrofuran 20 h; Ambient temperature;

1: 73 percent / Amberlyst 15; Et3N / CH2Cl2 / 2 h / 20 °C 2: 84 percent / ammonium acetate / ethanol View Scheme

1: 95 percent / 0.2 M aq. oxalic acid / 2 h / 90 °C 2: 1.) NH3, 2.) NH4Cl / 1.) MeOH, 4 deg C, 30 min, 2.) H2O, MeOH, RT, 24 h 3: 69 percent / 10percent aq. KOH / 24 h / Heating 4: 67 percent / H2 / 10percent Pd/C / aq. ethanol / 2 h / 760 Torr View Scheme

oxalic acid T=90°C; 2 h;