1: pyridinium chlorochromate 2: p-toluenesulfonic acid / benzene 4: tetra-n-butylammonium fluoride 5: 1.) d.HCl; 2.) triphenylphosphorane / 1.) in acetone; 2.) Wittig-reaction View Scheme

1.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 2.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 3.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 2.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 3.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 4.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 5.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 6.1: pyridine / CHCl3 / 3 h / 20 °C 7.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C 8.1: aq. hydrobromic acid / CHCl3; acetic acid / 1.5 h / 20 °C 8.2: 44 percent / tributyltin hydride; α,α'-azobis(isobutyronitrile) / benzene / 1 h / Heating View Scheme

1.1: 86 percent / chromium(VI) oxide; pyridine / CHCl3 / 12 h / 20 °C 2.1: butyllithium / tetrahydrofuran / 0.5 h / 0 °C 2.2: 77 percent / tetrahydrofuran / 2 h / 20 °C 3.1: conc. hydrochloric acid / tetrahydrofuran; methanol / 1 h / 20 °C 4.1: 1.4 g / pyridine; dimethylaminopyridine / 12 h / 20 °C 5.1: 87 percent / AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 50 h / 20 °C 6.1: pyridine / CHCl3 / 3 h / 20 °C 7.1: 1.8 g / K2CO3 / methanol; H2O / 15 h / 20 - 40 °C View Scheme