sodium tetrahydroborate in tetrahydrofuran; ethanol

1: 63 percent / NaOEt / 7 h / Heating 2: 98 percent / KOH / ethanol; H2O / 6 h / Heating 3: 95 percent / 170 °C 4: thionyl chloride / 0.75 h / Heating 5: 85 percent / AlCl3 / CS2 / 3 h / Heating 6: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 91 percent / sulfuric acid / H2O / 4 h / Heating 2: 84 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 4: 63 percent / NaOEt / 7 h / Heating 5: 98 percent / KOH / ethanol; H2O / 6 h / Heating 6: 95 percent / 170 °C 7: thionyl chloride / 0.75 h / Heating 8: 85 percent / AlCl3 / CS2 / 3 h / Heating 9: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 84 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 3: 63 percent / NaOEt / 7 h / Heating 4: 98 percent / KOH / ethanol; H2O / 6 h / Heating 5: 95 percent / 170 °C 6: thionyl chloride / 0.75 h / Heating 7: 85 percent / AlCl3 / CS2 / 3 h / Heating 8: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 2: 63 percent / NaOEt / 7 h / Heating 3: 98 percent / KOH / ethanol; H2O / 6 h / Heating 4: 95 percent / 170 °C 5: thionyl chloride / 0.75 h / Heating 6: 85 percent / AlCl3 / CS2 / 3 h / Heating 7: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 98 percent / KOH / ethanol; H2O / 6 h / Heating 2: 95 percent / 170 °C 3: thionyl chloride / 0.75 h / Heating 4: 85 percent / AlCl3 / CS2 / 3 h / Heating 5: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: thionyl chloride / 0.75 h / Heating 2: 85 percent / AlCl3 / CS2 / 3 h / Heating 3: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 85 percent / AlCl3 / CS2 / 3 h / Heating 2: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 95 percent / 170 °C 2: thionyl chloride / 0.75 h / Heating 3: 85 percent / AlCl3 / CS2 / 3 h / Heating 4: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme

1: 86 percent / ethanol; H2O / 0.75 h / Heating 2: 91 percent / sulfuric acid / H2O / 4 h / Heating 3: 84 percent / LiAlH4 / diethyl ether / 1 h / Heating 4: 72 percent / 48percent HBr, H2SO4 / 3 h / Heating 5: 63 percent / NaOEt / 7 h / Heating 6: 98 percent / KOH / ethanol; H2O / 6 h / Heating 7: 95 percent / 170 °C 8: thionyl chloride / 0.75 h / Heating 9: 85 percent / AlCl3 / CS2 / 3 h / Heating 10: 89 percent / NaBH4 / ethanol; tetrahydrofuran View Scheme