1: 1-Hydroxynon-8-yne With n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; Petroleum ether T=-78 - -30°C; 2: 1-n-heptylbromide in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=20°C; 12 h;

1.1: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / -78 - -30 °C 1.2: 4.17 g / + / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / 20 °C 2.1: 3.94 g / KNH(CH2)3NH2 / 0.5 h / 20 °C 3.1: n-BuLi / tetrahydrofuran; petroleum ether; hexamethylphosphoric acid triamide / -78 - -30 °C 3.2: 400 mg / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / 20 °C View Scheme

chromium(VI) oxide; sulfuric acid in acetone T=-10°C; 0.25 h;