lithium aluminium tetrahydride in diethyl ether Ambient temperature;

1: 100 percent / H2 / Pd/C / ethyl acetate / 12 h / 20 °C 2: 97 percent / LiAlH4 / tetrahydrofuran View Scheme

lithium aluminium tetrahydride in diethyl ether 2 h; Ambient temperature;

1: 6.6 g / aq. K2CO3 / 6 h / 20 °C 2: H2 / Pd/C / ethanol 3: 100 percent / LiAlH4 / diethyl ether / 0 - 20 °C View Scheme

1: aq. NaIO4; NaHCO3 / 1 h / 20 °C 2: 6.6 g / aq. K2CO3 / 6 h / 20 °C 3: H2 / Pd/C / ethanol 4: 100 percent / LiAlH4 / diethyl ether / 0 - 20 °C View Scheme

1: sulphuric acid / methanol / Ambient temperature 2: NaIO4, 5percent aq. NaHCO3 / 1 h / Ambient temperature 3: 10 N aq. K2CO3 / 16 h / Ambient temperature 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 2585.7 Torr 5: 50 percent / DIBAL-H / hexane; CH2Cl2 / 6 h / Ambient temperature View Scheme

Multistep reaction;