N-(dichloromethylene)-N,N-dimethylammonium chloride in dichloromethane T=0°C;

in dimethyl sulfoxide T=5°C; 2 h; Inert atmosphere;

in dimethyl sulfoxide T=10°C; 1 h;

1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=-30 - 20°C; Inert atmosphere;

toluene-4-sulfonic acid in dichloromethane T=25°C; 1 h;

sodium iodide in acetone Iodination; Heating;

1: 8.13 g / TsOH / CH2Cl2 / 7 h / 20 °C 2: 83 percent / PPh3; imidazole; iodine / benzene; diethyl ether / 1 h / 20 °C View Scheme

sodium iodide in acetone Substitution; 24 h; Heating;

1: phenylacetylene With n-butyllithium in tetrahydrofuran; hexane T=0°C; 1.5 h; Inert atmosphere; 2: 1-iodo-4-[(tetrahydropyran-2-yl)oxy]butane With N,N,N',N',N'',N''-hexamethylphosphoric triamide in tetrahydrofuran; hexane T=0 - 20°C; 12.5 h; Inert atmosphere; 3: With toluene-4-sulfonic acid in methanol; water T=20°C; 2 h; Inert atmosphere;

calcium carbonate in acetonitrile T=70°C; 50 h; Inert atmosphere;