sodium tetrahydroborate in diethyl ether 3 h; Ambient temperature;

1: NaBH4 / methanol 2: 94 percent / NaH / tetrahydrofuran 3: 8 percent / pentane / 3 h / -78 °C 4: TsOH / toluene / Heating 5: O3 / methanol 6: NaBH4 / methanol 7: pyridine 8: NaBH4 / dimethylsulfoxide View Scheme

1: KCN, 18-crown-6 / CH2Cl2 / 0.17 h 2: acetic acid / 5 h / 23 °C View Scheme

1: NaBH4 / methanol 2: 94 percent / NaH / tetrahydrofuran 3: 8 percent / pentane / 3 h / -78 °C 4: TsOH / toluene / Heating View Scheme

1: benzene / 12 h / Ambient temperature 2: MeSO3H / methanol / 12 h / Ambient temperature View Scheme