tetrabutyl ammonium fluoride in tetrahydrofuran T=0°C; 0.25 h;

1: 3.6 g / imidazole / dimethylformamide / 48 h / 38 °C 2: 67 percent / LiAlH4 / diethyl ether / 1.5 h / Heating 3: 95 percent / chromic oxide, pyridine / CH2Cl2; dimethylformamide / 1 h / Ambient temperature 4: 89 percent / sodium chlorite, 2-methyl-2-butene, sat. aq. potassium dihydrogen phosphate, t-BuOH / 5 h / Ambient temperature 5: 56 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C View Scheme

1: 95 percent / chromic oxide, pyridine / CH2Cl2; dimethylformamide / 1 h / Ambient temperature 2: 89 percent / sodium chlorite, 2-methyl-2-butene, sat. aq. potassium dihydrogen phosphate, t-BuOH / 5 h / Ambient temperature 3: 56 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C View Scheme

1: 89 percent / sodium chlorite, 2-methyl-2-butene, sat. aq. potassium dihydrogen phosphate, t-BuOH / 5 h / Ambient temperature 2: 56 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C View Scheme

1: 67 percent / LiAlH4 / diethyl ether / 1.5 h / Heating 2: 95 percent / chromic oxide, pyridine / CH2Cl2; dimethylformamide / 1 h / Ambient temperature 3: 89 percent / sodium chlorite, 2-methyl-2-butene, sat. aq. potassium dihydrogen phosphate, t-BuOH / 5 h / Ambient temperature 4: 56 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C View Scheme