1: 98 percent / LiAlH4 / diethyl ether / 20 °C 2: DMSO; (COCl)2; Et3N / CH2Cl2 / -78 °C 3: benzene / 60 °C 4: 89 percent / H2 / Pd/C / ethyl acetate / 20 °C 5: 92 percent / tetrahydrofuran / 0 °C 6: 91 percent / mCPBA; NaHCO3 / CH2Cl2 / 20 °C 7: 100 percent / LTMP; Et2AlCl / toluene / 0 °C 8: 96 percent / OsO4; NMO / tetrahydrofuran; H2O / 20 °C 9: NaIO4 / tetrahydrofuran; H2O / 20 °C 10: dimethylsulfoxide / 40 °C 11: LiAlH4 / tetrahydrofuran 12: DMSO; (COCl)2; Et3N / CH2Cl2 / -78 °C 13: dimethylsulfoxide / 40 °C 14: 85 percent / Ph2PLi / tetrahydrofuran / 50 °C View Scheme

lithium aluminium tetrahydride in diethyl ether T=20°C;