in chloroform T=65°C; 14 h;

in acetonitrile T=65°C; 24 h;

1: 1.) Et3N, 2.) 0.1 M aq. KCl / 1.) CHCl3, r.t., 6 h; 40 deg C, 12 h, 2.) r.t., 1 h 2: 47 percent / CHCl3 / 14 h / 65 °C View Scheme

1: H2 / 5percent Pd-C / ethanol 2: 98 percent / pyridine, DMAP 3: 90 percent / acetonitrile 4: PPTS / ethanol / 55 °C 5: Et3N / CH2Cl2 6: 1.) H2O / 2.) 65 deg C View Scheme

1: 1.) NaH / 1.) THF, r.t., 15 min; 60 deg C, 1.5 h, 2.) reflux, 36 h 2: HCl / methanol; CHCl3 / 1 h / Ambient temperature 3: 72 percent / Et3N / toluene / 60 h / 65 °C 4: 84 percent / 4-(dimethylamino)pyridine / CHCl3 / 36 h / Ambient temperature 5: HCl / methanol; CHCl3 / 1 h / Ambient temperature 6: 85 percent / acetonitrile / 6 h / Ambient temperature 7: 1.) Et3N, 2.) 0.1 M aq. KCl / 1.) CHCl3, r.t., 6 h; 40 deg C, 12 h, 2.) r.t., 1 h 8: 47 percent / CHCl3 / 14 h / 65 °C View Scheme

1: 84 percent / 4-(dimethylamino)pyridine / CHCl3 / 36 h / Ambient temperature 2: HCl / methanol; CHCl3 / 1 h / Ambient temperature 3: 85 percent / acetonitrile / 6 h / Ambient temperature 4: 1.) Et3N, 2.) 0.1 M aq. KCl / 1.) CHCl3, r.t., 6 h; 40 deg C, 12 h, 2.) r.t., 1 h 5: 47 percent / CHCl3 / 14 h / 65 °C View Scheme

1: 85 percent / acetonitrile / 6 h / Ambient temperature 2: 1.) Et3N, 2.) 0.1 M aq. KCl / 1.) CHCl3, r.t., 6 h; 40 deg C, 12 h, 2.) r.t., 1 h 3: 47 percent / CHCl3 / 14 h / 65 °C View Scheme

1: HCl / methanol; CHCl3 / 1 h / Ambient temperature 2: 85 percent / acetonitrile / 6 h / Ambient temperature 3: 1.) Et3N, 2.) 0.1 M aq. KCl / 1.) CHCl3, r.t., 6 h; 40 deg C, 12 h, 2.) r.t., 1 h 4: 47 percent / CHCl3 / 14 h / 65 °C View Scheme

1: HCl / methanol; CHCl3 / 1 h / Ambient temperature 2: 72 percent / Et3N / toluene / 60 h / 65 °C 3: 84 percent / 4-(dimethylamino)pyridine / CHCl3 / 36 h / Ambient temperature 4: HCl / methanol; CHCl3 / 1 h / Ambient temperature 5: 85 percent / acetonitrile / 6 h / Ambient temperature 6: 1.) Et3N, 2.) 0.1 M aq. KCl / 1.) CHCl3, r.t., 6 h; 40 deg C, 12 h, 2.) r.t., 1 h 7: 47 percent / CHCl3 / 14 h / 65 °C View Scheme