copper(l) iodide; potassium carbonate; sodium sulfite in water T=30°C; 4 h;

1: propargyl alcohol With copper(l) iodide; potassium carbonate; triethylamine in N,N-dimethyl-formamide 2 h; 2: 3-chloroprop-1-ene in N,N-dimethyl-formamide T=50 - 55°C; 8 h; Further stages.;

hydrogenchloride; sodium hydroxide; sodium chloride in methanol

copper(l) iodide; potassium carbonate; triphenylphosphine in N,N-dimethyl-formamide 15 h; Heating;

CuBr-Me2S complex in tetrahydrofuran T=0 - 20°C; 13 h; Yield given;

copper

1: mercury (II)-sulfate; water 2: hydrazine hydrate; alkalihydrazide View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 3 h; Heating;

1: 94 percent / KOH / diethyl ether / 4 h 2: EtMgBr, CuBr*Me2S / tetrahydrofuran / 1.) 50 deg C, 30 min; 0 deg C, 5 min, 2.) 0 deg C to r.t., 10 h 3: 1.) K3Fe(CN)6, K2CO3, OsO4, H2O, 2.) Dowex 50 x 8 - 100 ion-exchange resin / 1.) t-BuOH, r.t., 48 h, 2.) MeOH, r.t., 13 h 4: conc. H2SO4, molecular sieves 4A, Na2SO4 / 13 h / Ambient temperature 5: 87 percent / H2, ethylenediamine / P-2 Ni catalyst / ethanol / 5 h / 23 °C 6: 82 percent / pyridine / CH2Cl2 / 8 h / 0 °C 7: CaCO3 / acetonitrile / 48 h / 90 °C 8: 73 percent / NaHMDS / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) -78 deg C to r.t., 3 h 9: 90 percent / 4 N aq. HCl, methylene blue / tetrahydrofuran / 0.5 h 10: 0.8 M aq. NaIO4, 60-200 mesh SiO2 / CH2Cl2 / 0.08 h / Ambient temperature 11: NaHMDS / 1.) THF, -75 deg C, 2.) CH2Cl2, -75 deg C to r.t., 4 h View Scheme

1: 90 percent / H2 / Lindlar's catalyst, quinoline / hexane 2: 90 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 2 h 3: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 16 h 4: 60 percent / 10percent sodium hydroxide / methanol / 24 h 5: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C View Scheme