propane-1-thiol; zinc dibromide in dichloromethane T=20°C; 0.116667 h; Inert atmosphere;

sodium borohydride; sulfuric acid in water; N,N-dimethyl-formamide

1: 90 percent / pyridine / 20 °C 2: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 3: Jones reagent / acetone 4: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

1: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 2: 90 percent / pyridine / 20 °C 3: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 4: Jones reagent / acetone 5: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

1: methanol; diethyl ether 2: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3: 90 percent / pyridine / 20 °C 4: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 5: Jones reagent / acetone 6: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

1: Jones reagent / acetone 2: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

1: 85 percent / Candida antarctica B lipase / ethanol / 3 h / 30 °C 2: Jones reagent / acetone 3: 0.06 g / KOH / methanol; H2O / 3 h / 50 °C View Scheme

1.1: pyridinium bromide perbromide / ethanol; water / 5.25 h / 24 - 27 °C / |Inert atmosphere; |Large scale 2.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 110 - 115 °C / |Inert atmosphere 3.1: ozone / methanol / 6 h / -40 - -30 °C / |Inert atmosphere; |Large scale 4.1: sodium hydroxide / ethanol; water / 8 - 9 °C / |Inert atmosphere 4.2: 1 h / 5 - 7 °C 4.3: 8.75 h / 1 - 9 °C View Scheme

1.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 3 h / 110 - 115 °C / |Inert atmosphere 2.1: ozone / methanol / 6 h / -40 - -30 °C / |Inert atmosphere; |Large scale 3.1: sodium hydroxide / ethanol; water / 8 - 9 °C / |Inert atmosphere 3.2: 1 h / 5 - 7 °C 3.3: 8.75 h / 1 - 9 °C View Scheme

1.1: ozone / methanol / 6 h / -40 - -30 °C / |Inert atmosphere; |Large scale 2.1: sodium hydroxide / ethanol; water / 8 - 9 °C / |Inert atmosphere 2.2: 1 h / 5 - 7 °C 2.3: 8.75 h / 1 - 9 °C View Scheme