ethanol; sodium hydride in diethyl ether Heating;

1: 81 percent / NaH, EtOH / diethyl ether / Heating 2: 94 percent / K2CO3, H2O / methanol / 48 h / Ambient temperature 3: Et3N / tetrahydrofuran / 1 h / Ambient temperature 4: tetrahydrofuran / 3 h / Ambient temperature 5: 95 percent / 4 N H2SO4 / tetrahydrofuran / 4 h / Heating 6: 81 percent / LiAlH4 / diethyl ether 7: 1.) Et3N / 1.) CH2Cl2, 10 min, 2.) CH2Cl2, RT, 1 h 8: 62 percent / 15-crown-5 / dimethylsulfoxide / Ambient temperature 9: 83 percent / i-Bu2AlH / benzene; hexane / 3 h / 0 °C 10: 76 percent / CrO3, aq. H2SO4 / acetone / 0.5 h / Ambient temperature View Scheme

1.1: 80 percent / NaH / diethyl ether 2.1: 91 percent / K2CO3 / methanol; H2O 3.1: isobutylchloroformate; triethylamine / tetrahydrofuran / 0.25 h / 0 °C 3.2: 96 percent / tetrahydrofuran / 12 h / 20 °C View Scheme

1: 80 percent / NaH / diethyl ether 2: 91 percent / K2CO3 / methanol; H2O View Scheme