sodium hydroxide; Ni(OAr)2*4H2O; hydrogen; ethylenediamine in ethanol Ambient temperature;

sodium chloride in water; dimethyl sulfoxide T=180°C; 8 h;

1: 1-bromo-hexane With triphenylphosphine T=160°C; 8 h; 2: ethyl 7-oxo-4(E)-heptenoate With potassium tert-butylate in tetrahydrofuran T=-70°C; Wittig reaction; 2 h; Further stages.;

propionic acid T=140°C; 1 h;

1: 68 percent / propionic acid / 2 h / 136 - 139 °C 2: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature View Scheme

1: 1) LiNH2 / 1) liq.NH3, -33 deg C, 2 h, 2) THF, -33 deg C, 0.5 h 2: 65 percent / propionic acid / 2 h / 138 °C 3: 80 percent / H2, quinoline / Pd-CaCO3 / hexane / 760 Torr View Scheme

1: 85 percent / hydrogen, triethylamine / P(2)-Ni / ethanol 2: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating 3: 83 percent / propionic acid / 1 h / 140 °C View Scheme

1: 1.) BuLi / 1.) THF, HMPT, hexane, 1 h, 2.) THF, HMPT, hexane, overnight 2: 77 percent / PBr3, pyridine / diethyl ether / 1.) -15 deg C, 2 h, 2.) room temp., 3 h, then 30 deg C, 45 min 3: 1.) Mg / 1.) Et2O, 2.) Et2O, -15 deg C, 0.5 h, -15 to 0 deg C, 0.5 h 4: 68 percent / propionic acid / 2 h / 136 - 139 °C 5: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature View Scheme

1: 1.) Mg / 1.) Et2O, 2.) Et2O, -15 deg C, 0.5 h, -15 to 0 deg C, 0.5 h 2: 68 percent / propionic acid / 2 h / 136 - 139 °C 3: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature View Scheme

1: 77 percent / PBr3, pyridine / diethyl ether / 1.) -15 deg C, 2 h, 2.) room temp., 3 h, then 30 deg C, 45 min 2: 1.) Mg / 1.) Et2O, 2.) Et2O, -15 deg C, 0.5 h, -15 to 0 deg C, 0.5 h 3: 68 percent / propionic acid / 2 h / 136 - 139 °C 4: 90 percent / NaB4, aq. NaOH, Ni(OAr)2*4H2O, ethylenediamine, H2 / ethanol / Ambient temperature View Scheme