sodium iodide in N,N-dimethyl-formamide T=20°C; 5 h;

sodium iodide in N,N-dimethyl-formamide T=65°C; 42 h;

1: (phenylsulfonyl)methane With n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=-78°C; 0.5 h; 2: 1-bromo-octan-8-ol in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=-78 - 20°C; 8 h; Further stages.;

2: powdered sodium hydroxide / dioxane / 14 h / Ambient temperature; further solvents were also used 3: Adogen, sodium dithionite, NaHCO3 / cyclohexane; H2O / 2 h / Heating View Scheme

2: powdered sodium hydroxide / dioxane / 14 h / Ambient temperature; further solvents were also used 3: Adogen, sodium dithionite, NaHCO3 / cyclohexane; H2O / 2 h / Heating 4: pyridine / 4 h / Ambient temperature View Scheme