tetrabutyl ammonium fluoride in tetrahydrofuran

1: LiSEt / dimethylformamide / 18 h / Heating 2: imidazole / dimethylformamide / 3.5 h / Ambient temperature 3: 70 percent / Zn / benzene / 1 h / Heating 4: 46 percent / SOCl2 / pyridine / 0.25 h / Ambient temperature 5: 82 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 6: 69 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: imidazole / dimethylformamide / 3.5 h / Ambient temperature 2: 70 percent / Zn / benzene / 1 h / Heating 3: 46 percent / SOCl2 / pyridine / 0.25 h / Ambient temperature 4: 82 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 5: 69 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: 70 percent / Zn / benzene / 1 h / Heating 2: 46 percent / SOCl2 / pyridine / 0.25 h / Ambient temperature 3: 82 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 4: 69 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: 82 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 2: 69 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: 46 percent / SOCl2 / pyridine / 0.25 h / Ambient temperature 2: 82 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 3: 69 percent / n-Bu4NF / tetrahydrofuran View Scheme