1: 81 percent / LiAlH4 / tetrahydrofuran / 0.5 h / cooling 2: 81 percent / MnO2 / CH2Cl2 / 48 h / 20 °C View Scheme

1: 98 percent / LiAlH4 / diethyl ether / 4 h / Heating 2: 90 percent / MnO2 / benzene / Heating 3: 80 percent / piperidine acetate / toluene / Heating 4: 80 percent / LiAlH4 / tetrahydrofuran / Heating 5: 50percent aq. sulphuric acid / a. water removed, b. 130-140 deg C (15mm), 2h 6: 10percent aq. NaOH / Heating 7: 65 percent / Heating 8: POCl3 / toluene / 95 °C 9: NaBH4 / methanol / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether 4 h; Heating;

in tetrahydrofuran