1: 78.2 percent / benzene; pyridine / 1) water bath, overnight, 2) reflux, 3 h 2: 1) Cu, 2) KOH / 1) DMF, reflux, 5 h, 2) aq EtOH, reflux, 5 h View Scheme

1: 5 h / Heating 2: 81 percent / Cu / dimethylformamide / 12 h / Heating 3: KOH / methanol / 15 h / Heating View Scheme

1: 78.2 percent / benzene; pyridine / 1) water bath, overnight, 2) reflux, 3 h 2: 1) Cu, 2) LiAlH4 / 1) DMF, reflux, 5 h, 2) Et2O, reflux, 3 h View Scheme

2: 74 percent / SOCl2 / benzene; CH2Cl2 / 0 °C 3: 1.) NaH / 1.) DMF, 50 deg C, 3 h, 2.) 50 deg C, 5 h 4: 1.) Mg / 1.) Et2O <dibromoethane>, benzene, reflux, 2.) reflux, 3.25 h 5: 2.) aqueous 20 percent NaOH / 1.) 12 h, 25 deg C, 2.) MeOH, 24 h, reflux 6: BH3*THF / tetrahydrofuran / 1.a) 10 min, 0 deg C, b) 1 h, 25 deg C, 2.) THF/H2O = 2:1, 15 min, 25 deg C View Scheme

thionyl chloride 21 h; Heating;

1: 94 percent / 2-methyl-2-butene, aq. NaClO2, NaH2PO4*H2O / 2-methyl-propan-2-ol / Ambient temperature 2: (COCl)2, DMF / CH2Cl2 / Ambient temperature View Scheme

1: 88 percent / Co(Ac)2*H2O, 2-butanone / acetic acid / 9 h / 90 - 100 °C 2: 97 percent / SOCl2 / 21 h / Heating View Scheme

1: 1.) N4(CH2)6; 2.) HOAc/HCl 2: 71 percent / KMnO4 / acetone; H2O / 2 h / 40 °C 3: SOCl2 / toluene / 3 h / Heating View Scheme

1: 91 percent / Br2 / CS2 2: 79 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating; Irradiation 3: 1.) N4(CH2)6; 2.) HOAc/HCl 4: 71 percent / KMnO4 / acetone; H2O / 2 h / 40 °C 5: SOCl2 / toluene / 3 h / Heating View Scheme

1: 5 h / Heating 2: 81 percent / Cu / dimethylformamide / 12 h / Heating View Scheme