1: 31 percent / f.HNO3, Ac2O / 1.) from -30 to -40, 1 h, 2.) 0 deg C, 2 h 2: 42 percent / H2, gl.AcOH / 10percent Pd/C / methanol / 12 h / 2280 Torr View Scheme

sodium methylate in methanol 4 h; Heating;

1.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 140 °C 2.1: acetic acid; sulfuric acid / 2 h / 120 °C 2.2: |Cooling with ice 3.1: [{(η5-C5Me5)IrCl}2(μ-Cl)2]; 2-hydroxy-pyridine / 2,2,2-trifluoroethanol / 120 h / 100 °C / |Inert atmosphere View Scheme

4 h; Heating;