1: 61 percent / 50percent aq. acetic acid / 2 h / 200 °C 2: NaH / tetrahydrofuran / 2 h / 67 °C 3: 63 percent / benzene / 0.17 h / Heating 4: 66 percent / bis(benzonitrile)palladium(II) chloride, air / 2-methyl-propan-2-ol / 116 °C 5: 100 percent / aluminum isopropoxide / propan-2-ol / Heating 6: pyridine / 15 h / 20 °C 7: tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h / 100 °C 8: trifluoroacetic acid / CH2Cl2 / 0.5 h 9: 99 percent / N-methylmorpholine, osmium tetraoxide / tetrahydrofuran; H2O / 24 h / 20 °C 10: 1.) methyl sulfide, N-chlorosuccinimide, 2.) triethylamine / 1.) dichloromethane, -40 deg C, 1 h, 2.) from -40 to 20 deg C, 1.5 h 11: 97 percent / trifluoromethanesulfonic acid / CH2Cl2 / 24 h 12: 88 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / Heating View Scheme

1: 68 percent / Et4NOTs / propan-2-ol / 25 °C / electroreduction (Sn-cathode) 2: LAH / tetrahydrofuran / 1 h / Ambient temperature 3: 1) MsCl, Et3N, 2) LAH / 1) CH2Cl2, 0 deg C, 2 h, 2) THF, reflux, 6 h View Scheme