1: 90 percent / i-Bu2AlH / diethyl ether / -70 °C 2: 60 percent / MeSO2Cl, LiCl, s-collidine / dimethylformamide / 2 h / 0 °C 3: 70 percent / n-BuLi / tetrahydrofuran; dimethylsulfoxide / 16 h / 20 °C 4: 95 percent / pyridinium toluene-p-sulphonate / methanol / 8 h / 60 °C 5: 42 percent / 2-chloro-1-methylpyridinium iodide / acetonitrile / 18 h / 80 °C 6: LDA / tetrahydrofuran / -100 - 20 °C 7: K2CO3, MeOH, H2O / 2 h / 20 °C 8: (COCl2), DMF / diethyl ether / 2 h / 0 - 20 °C 9: diethyl ether / 16 h / 0 - 20 °C 10: Et3N / PhCO2Ag / 16 h / 20 °C 11: 90 percent / 40 percent aq. HF / tetrahydrofuran / 6 h / 20 °C 12: 62 percent / CrO3 in H2SO4 13: Me3SiI, C5H5N / CHCl3 / 5 h / 60 °C 14: KOH, H2O / 16 h / 20 °C View Scheme