5 palladium on charcoal; hydrogen in methanol T=25°C; P=22502.3 Torr; 5 h;

1.1: propionic acid / 140 °C 1.2: 85 percent / NaOH / ethanol / Heating 2.1: 72 percent / LiAlH4 / tetrahydrofuran 3.1: p-TsCl; pyridine 3.2: 67 percent / LiAlH4 / tetrahydrofuran / Heating 4.1: O3 / methanol; CH2Cl2 / -78 °C 4.2: 79 percent / NaBH4 / methanol; CH2Cl2 / -78 °C 5.1: p-TsCl; pyridine 5.2: NaN3 / aq. ethanol / 10 h / Heating 6.1: LiAlH4 / diethyl ether / Heating View Scheme

5 palladium on charcoal; hydrogen in methanol T=25°C; P=22502.3 Torr; 5 h;