1: 87 percent / K2CO3 / acetone / 5 h / Heating 2: 63 percent / N,N-diethylaniline / 2 h / Heating 3: 1.) O3, 2.) H2 / 2.) 10percent Pd/CaCO3 / 1.) EtOAc, 2.) EtOAc 4: 85percent aq. H3PO4 / 0.5 h / 100 °C View Scheme

1: 1.) O3, 2.) H2 / 2.) 10percent Pd/CaCO3 / 1.) EtOAc, 2.) EtOAc 2: 85percent aq. H3PO4 / 0.5 h / 100 °C View Scheme

phosphoric acid T=100°C; 0.5 h; Yield given;

1: 63 percent / N,N-diethylaniline / 2 h / Heating 2: 1.) O3, 2.) H2 / 2.) 10percent Pd/CaCO3 / 1.) EtOAc, 2.) EtOAc 3: 85percent aq. H3PO4 / 0.5 h / 100 °C View Scheme