1: 1.) BuLi, 2.) Br2 2: 84 percent / Et3N 3: 1.) ZnCl2, 3.) PhMe2SiCl View Scheme

1: 5-phenyl-1-pentyn-3-ol With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: methyl iodide With N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane T=-78 - 20°C;

1: 85 percent / DMAP; pyridine / 0.5 h / 20 °C 2: H2O / NaAuCl4*2H2O / methanol / 2 h / Heating 3: SmI2; ethyl acrylate; MeOH View Scheme

1: With IPNBSH; triphenylphosphine; diethylazodicarboxylate in tetrahydrofuran T=0 - 23°C; Mitsunobu reaction; 2 h; 2: in 2,2,2-trifluoroethanol; water T=23°C; 2 h;