1: 78 percent / HCl (2N) / tetrahydrofuran / Ambient temperature 2: 92 percent / 4,4-dimethylaminopyridine / pyridine / 3 h / 100 °C 3: KH (22percent) / benzene / Ambient temperature 4: 92 percent / p-toluenesulfonic acid monohydrate / methanol / Heating 5: 1.) NEt3; 2.) KCl (0.1N) / 1.) CHCl3, room temp., 6h; 40 deg C, 12 h; 2.) 1 h 6: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h 7: 95 percent / H2 / palladium black / ethanol / 72 h / 50 °C / 760 Torr 8: 93 percent / pyridine / 2 h / 70 °C View Scheme

in methanol

1: 78 percent / HCl (2N) / tetrahydrofuran / Ambient temperature 2: 92 percent / 4,4-dimethylaminopyridine / pyridine / 3 h / 100 °C 3: KH (22percent) / benzene / Ambient temperature 4: 92 percent / p-toluenesulfonic acid monohydrate / methanol / Heating 5: 1.) NEt3; 2.) KCl (0.1N) / 1.) CHCl3, room temp., 6h; 40 deg C, 12 h; 2.) 1 h View Scheme

hydrogenchloride in tetrahydrofuran Ambient temperature;