hydrogen; 5percent Pd/C in methanol T=30°C; P=3040.2 Torr; 8 h;

1.1: 93 percent / K2CO3; 18-crown-6 / acetonitrile / Heating 2.1: O3 / -78 °C 2.2: p-TsOH; Me2S / methanol / 0 - 20 °C 2.3: 98 percent / aq. HClO4 / tetrahydrofuran / 7 h / 0 - 20 °C 3.1: 90 percent / H2 / 5percent Pd/C / methanol / 8 h / 30 °C / 3040.2 Torr View Scheme

1.1: O3 / -78 °C 1.2: p-TsOH; Me2S / methanol / 0 - 20 °C 1.3: 98 percent / aq. HClO4 / tetrahydrofuran / 7 h / 0 - 20 °C 2.1: 90 percent / H2 / 5percent Pd/C / methanol / 8 h / 30 °C / 3040.2 Torr View Scheme