lithium aluminium tetrahydride in diethyl ether 1 h; Heating;

1: 1.) C2H5MgBr, CuCN / 1.) THF, reflux, 30 min, 2.) THF, 25 deg C, 14 h 2: 96 percent / conc. H2SO4 / methanol / 16 h / 25 °C 3: 79 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 25 °C 4: 98 percent / diethyl ether; tetrahydrofuran / 30 h / Heating 5: 91 percent / propionic acid / 1 h / 138 °C 6: 92 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

1: 1.) C2H5MgBr, CuCN / 1.) THF, reflux, 30 min, 2.) THF, 25 deg C, 14 h 2: 96 percent / conc. H2SO4 / methanol / 16 h / 25 °C 3: 79 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 25 °C 4: 98 percent / diethyl ether; tetrahydrofuran / 30 h / Heating 5: 91 percent / propionic acid / 1 h / 138 °C 6: 92 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

1: 79 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 25 °C 2: 98 percent / diethyl ether; tetrahydrofuran / 30 h / Heating 3: 91 percent / propionic acid / 1 h / 138 °C 4: 92 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

1: 98 percent / diethyl ether; tetrahydrofuran / 30 h / Heating 2: 91 percent / propionic acid / 1 h / 138 °C 3: 92 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

1: 91 percent / propionic acid / 1 h / 138 °C 2: 92 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme

1: 96 percent / conc. H2SO4 / methanol / 16 h / 25 °C 2: 79 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 25 °C 3: 98 percent / diethyl ether; tetrahydrofuran / 30 h / Heating 4: 91 percent / propionic acid / 1 h / 138 °C 5: 92 percent / LiAlH4 / diethyl ether / 1 h / Heating View Scheme