1: 83 percent / C2H5ONa / ethanol; CHCl3 / 1) C2H5ONa, C2H5OH, 0 deg C, 30 min, 2) chloroform, room temperature, 15 h 2: 1) C2H5ONa 2) hydrochloric acid / 1) reflux, 14 h, 2) reflux, 3 h 3: 50 percent / 48percent aq. HBr / 19 h / Heating 4: 81 percent / K2CO3 / acetone / 2 h / Heating 5: 47 percent / C2H5ONa / toluene / 14 h / Heating 6: 90 percent / Cu powder / pyrolysis View Scheme

potassium carbonate in acetone 15 h; Heating;

1: 84 percent / K2CO3 / acetone / 15 h / Heating 2: 91 percent / C2H5ONa / toluene / 18 h / Heating View Scheme

1: 83 percent / C2H5ONa / ethanol; CHCl3 / 1) C2H5ONa, C2H5OH, 0 deg C, 30 min, 2) chloroform, room temperature, 15 h 2: 1) C2H5ONa 2) hydrochloric acid / 1) reflux, 14 h, 2) reflux, 3 h 3: 50 percent / 48percent aq. HBr / 19 h / Heating 4: 81 percent / K2CO3 / acetone / 2 h / Heating 5: 47 percent / C2H5ONa / toluene / 14 h / Heating View Scheme

1: 84 percent / K2CO3 / acetone / 15 h / Heating 2: 91 percent / C2H5ONa / toluene / 18 h / Heating 3: HCl / H2O / 3 h / Heating 4: NaBH4 / methanol / 0.5 h / Ambient temperature 5: 94 percent / H3PO4 (85percent) / 15 h / 170 - 180 °C View Scheme

ammonia T=110°C;

1: 65 percent / K2CO3 / acetone / 6 h / Heating 2: C2H5ONa / toluene / 17 h / Heating View Scheme

1: 83 percent / C2H5ONa / ethanol; CHCl3 / 1) C2H5ONa, C2H5OH, 0 deg C, 30 min, 2) chloroform, room temperature, 15 h 2: 1) C2H5ONa 2) hydrochloric acid / 1) reflux, 14 h, 2) reflux, 3 h 3: 50 percent / 48percent aq. HBr / 19 h / Heating View Scheme

sulfuric acid in benzene 40 h; Heating;

ethanol; sulfuric acid