sodium iodide in acetone 24 h; Heating;

1: 95 percent / NaI / acetone / 24 h / Heating 2: 1) t-BuLi / 1) Et2O, -78 deg C, 1 h 3: 1) oxalyl chloride, DMSO, 2) Et3N / 1) CH2Cl2, -60 deg C, 15 min, 2) 5 min View Scheme

dipyridinium dichromate; magnesium Multistep reaction;

1: furan With n-butyllithium in tetrahydrofuran T=-78 - 0°C; 3 h; 2: 1-bromo-3-chloro-propane in tetrahydrofuran T=20°C; 16 h;

tetrachloromethane; triphenylphosphine T=70°C; 1 h;

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / |Inert atmosphere 1.2: 2 h / -78 - 20 °C / |Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / |Inert atmosphere 3.1: AuBr3; sodium chloride / water / 0.5 h / 20 °C / |Darkness; |Sealed tube View Scheme

T=120°C;

1: 1.) Mg / 1.) THF, reflux 2.) RT 2: 79 percent / Br2, Na2CO3 / methanol / -30 °C 3: 75 percent / H2O / 0.5 h / 45 °C 4: I2 / diethyl ether / 0.17 h / Ambient temperature 5: 51 percent / KOtBu / tetrahydrofuran / 0 °C 6: 65 percent / NaBH4 / methanol / 0 °C View Scheme