1: 89 percent / benzene / 6 h / Heating 2: 18 percent / diethyl ether / 15 h / 20 °C View Scheme

tert-butyl alcohol in tetrahydrofuran T=20°C; 15 h;

1: H2 / Pd/C 2: LiAlH4 / tetrahydrofuran 3: pyridine 4: t-BuOK / dimethylsulfoxide View Scheme

1: 94 percent / H2 / 10percent Pd-C / methanol / 2585.7 Torr 2: 75 percent / 4-dimethylaminopyridine / pyridine / 15 h / 20 °C 3: 50 percent / t-BuOH / tetrahydrofuran / 15 h / 20 °C View Scheme

1: 88 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.) 0 deg C, 3 h, 2.) 20 deg C, 15 h 2: 94 percent / H2 / 10percent Pd-C / methanol / 2585.7 Torr 3: 75 percent / 4-dimethylaminopyridine / pyridine / 15 h / 20 °C 4: 50 percent / t-BuOH / tetrahydrofuran / 15 h / 20 °C View Scheme

1: 75 percent / 4-dimethylaminopyridine / pyridine / 15 h / 20 °C 2: 50 percent / t-BuOH / tetrahydrofuran / 15 h / 20 °C View Scheme

1: LiAlH4 / tetrahydrofuran 2: pyridine 3: t-BuOK / dimethylsulfoxide View Scheme