1: 100 percent / aq. sodium hydroxide / tetrahydrofuran / 1 h 2: 94 percent / diborane / tetrahydrofuran / 1) -20 deg C, 3 h; 2) -10 deg C, 3 h; 3) 0 deg C, 3 h; 4) 25 deg C, 4.5 h 3: 76 percent / imidazole / dimethylformamide / 18 h / Ambient temperature 4: 46 percent / thionyl chloride, pyridine / benzene / 0.42 h / Ambient temperature 5: 1.) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 10 min, -25 deg C, 10 min; 2) -23 deg C, 10 min 6: pyridine / CH2Cl2 / 4.5 h / Ambient temperature 7: 77 percent / 1,5-diazobicyclo<5.4.0>undec-5-ene / benzene / 0.67 h 8: 67 percent / Dowex 50W-X8 (H+) / CHCl3 / 3 h 9: 5.0 mg / pyridine, 4-dimethylaminopyridine / tetrahydrofuran / 43 h 10: 81 percent / Dowex 1-X8 (OH(1-)), methanol / 2 h / 0 °C View Scheme