1: H2, quinoline / Pd-BaSO4 / methanol 2: (i) Br2, CCl4, (ii) H2, Et3N, Raney-Ni, MeOH View Scheme

1: propargyl alcohol With ferric nitrate; ammonia; lithium in tetrahydrofuran T=-33°C; 1 h; Inert atmosphere; 2: 7-bromoheptanoic acid in tetrahydrofuran T=-33°C; 4 h; Inert atmosphere;

in tetrahydrofuran; ammonia T=-40°C; 20 h;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; lithium amide 1.) liq. NH3, from -50 deg C to -40 deg C, 0.5 h, 2.) THF, liq. NH3, a) -33 deg C, 1 h, b) RT, 4 h; Yield given. Multistep reaction;

1: 93 percent / sodium, NH3 (liquid) / tetrahydrofuran / 2 h / -33 °C 2: 100 percent / diethyl ether View Scheme