tetra-(n-butyl)ammonium iodide; potassium carbonate in butanone 8 h; Heating;

sodium iodide in acetone Iodination;

1: K2CO3; tetrabutylammonium iodide / butan-2-one / 8 h / Heating 2: 11.9 g / aq. KOH / ethanol / 2 h / Heating View Scheme

N-Trimethylamine hydrochloride; triethylamine in acetonitrile T=0 - 5°C; 1 h;

Tosylation;

in dimethyl sulfoxide T=25°C; 1.5 h;

1.1: Mg / tetrahydrofuran 1.2: Li2CuCl4 / tetrahydrofuran 2.1: 100 percent / CH2Cl2 / 0.17 h / 0 °C 3.1: 72 percent / t-BuOK; 18-crown-6 / petroleum ether / 2 h / Heating 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 4.2: tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.25 h / -78 °C 5.1: 97 percent / PtO2 / ethyl acetate / 12 h / 20 °C 6.1: 80 percent / HCl; H2O / methanol / 12 h / 60 °C 7.1: 71 percent / DCC / CH2Cl2 / 12 h 8.1: NH3; H2O / CHCl3; methanol / 12 h / 20 °C 9.1: H2O2; H2O / 12 h / 20 °C View Scheme

in dimethyl sulfoxide T=20°C;