1: thien-3-yl bromide With n-butyllithium in tetrahydrofuran; hexane T=-40 - 20°C; 2: n-decyl disulfide in tetrahydrofuran; hexane T=20°C; 2 h;

1.1: 89 percent / DMSO / 19 h / Heating 2.1: n-BuLi / hexane; tetrahydrofuran / -40 - 20 °C 2.2: 75 percent / hexane; tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: n-BuLi; diisopropylamine / hexane; tetrahydrofuran / 1.17 h / -78 - -40 °C 1.2: trimethyl borate / hexane; tetrahydrofuran / -40 - 20 °C 1.3: 83 percent / sodium sulfate / diethyl ether / 0.5 h / 20 °C 2.1: tetrakis(triphenylphosphine)palladium(0) / 1,2-dimethoxy-ethane / 0.17 h / 20 °C 2.2: 79 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 4 h / Heating 3.1: POCl3 / 1 h / 20 °C 3.2: 92 percent / 12 h / 70 °C 4.1: 92 percent / AlCl3; LiAlH4 / diethyl ether / 2 h / 20 °C 5.1: 92 percent / aq. H2O2; acetic acod / CH2Cl2 / 3 h / 30 °C View Scheme