1: aq. NaOH / ethanol / 3 h / Heating 2: LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme

1: 70 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 2: 93 percent / magnesium oxide / H2O / 3 h / 0 °C 3: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature 4: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h 5: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature 6: 62 percent / sodium hydride / tetrahydrofuran / Ambient temperature 7: 70 percent / acetic acid, water / tetrahydrofuran / 1 h / Ambient temperature 8: 100 percent / H2 / 10percent Pd/C / ethanol / 2585.7 Torr View Scheme

lithium aluminium tetrahydride in diethyl ether 5 h; Heating;

1: 70 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 2: 93 percent / magnesium oxide / H2O / 3 h / 0 °C 3: 60 percent / 90percent aq. trifluoroacetic acid / 0.08 h / Ambient temperature 4: 80 percent / pyridine / 1.) 0 deg C, 1 h, 2.) 8 deg C, 40 h 5: 100 percent / 4-methylbenzenesulfonic acid / diethyl ether / Ambient temperature 6: 62 percent / sodium hydride / tetrahydrofuran / Ambient temperature 7: 70 percent / acetic acid, water / tetrahydrofuran / 1 h / Ambient temperature View Scheme