1: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h 2: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 3: 83 percent / xylene / 10 h / Heating 4: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 5: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 20 h / 20 °C 2: PDC / dichloromethane / 20 h / 20 °C 3: sodium hydride / tetrahydrofuran / 18 h / 0 - 20 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: 88.7 percent / LiAlH4 / tetrahydrofuran / 20 h / 0 °C 2.1: 61 percent / p-TsCl; Et3N; 4-dimethylaminopyridine / CH2Cl2 / 12 h / 20 °C 3.1: 86.1 percent / NaI / 6 h / 135 °C 4.1: NaH / tetrahydrofuran / 2 h / -55 - 0 °C 4.2: 50.8 percent / tetrahydrofuran / 24 h / -55 - 0 °C 5.1: 79 percent / hydrochloric acid / ethanol / 26 h / 20 °C View Scheme

1: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h 2: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 3: 83 percent / xylene / 10 h / Heating 4: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 5: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature View Scheme

1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO2H / 1 h / Heating View Scheme

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

Multi-step reaction with 3 steps 1: 100 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature2: 87 percent / PPh3, CCl4 / 2 h / 110 °C3: 86 percent / 5 h / 100 °C  

Multi-step reaction with 4 steps 1: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h2: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C3: 83 percent / xylene / 10 h / Heating4: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h