1: K2CO3 / methanol / 1 h / 20 °C 2: 95 percent / BCl3*SMe2 / CH2Cl2 / 0.25 h / 20 °C View Scheme

n-butyllithium; iodine; 1,1,1,3,3,3-hexamethyl-disilazane in tetrahydrofuran T=-78°C; 0.166667 h;

1.1: K2CO3 / methanol / 1 h / 20 °C 2.1: 95 percent / BCl3*SMe2 / CH2Cl2 / 0.25 h / 20 °C 3.1: 96 percent / nBu3P / tetrahydrofuran / 3 h / 20 °C 4.1: silica gel / 72 h / 20 °C 4.2: 66 percent / aq. ammonium cerium nitrate / diethyl ether / 1 h / 20 °C 5.1: 80 percent / OsO4; pyridine / 24 h 6.1: 95 percent / H2O2 / tetrahydrofuran / 16 h 7.1: 4 Angstroem molecular sieves 8.1: NaH; pyridine / 1 h / 20 °C View Scheme