lithium aluminium tetrahydride in diethyl ether 1.) 0 deg C, 5 min, 2.) 20 deg C, 30 min;

(saponification);

1.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 2.1: n-butyllithium; N-cyclohexyl-N-isopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 2.2: 1 h / -78 °C / Inert atmosphere 3.1: palladium 10 on activated carbon / triglyme (triethylene glycol dimethyl ether) / 4 h / 240 °C / Inert atmosphere 4.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: methanesulfonic acid / dichloromethane / 0.5 h / 20 °C / Cooling with ice View Scheme

1: (saponification) 2: (i) SOCl2, Py, Et2O, (ii) SnCl4, benzene View Scheme

1: 94 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 5 min, 2.) 20 deg C, 30 min 2: 89 percent / (COCl)2, DMSO, Et3N / CH2Cl2 View Scheme

1.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 2.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 2.2: 120 - 215 °C View Scheme

1: LiAlH4; diethyl ether 2: red phosphorus; aqueous HBr 3: KCN 4: aqueous H2SO4; acetic acid View Scheme