sodium tetrahydroborate in methanol T=0 - 20°C; 0.166667 h;

1-trans-IODO-4-CYCLOHEXYL in N,N-dimethyl-formamide 78 h; RefluxInert atmosphere;

sodium tetrahydroborate in N,N-dimethyl-formamide T=20°C; 2 h;

1.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 18 h / Reflux 3.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere 3.2: 0.83 h / -78 - 20 °C / Inert atmosphere 3.3: 0 °C / pH 5 - 6 / Inert atmosphere 4.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere 5.1: hydrogenchloride / methanol; water / 16 h / 0 °C / pH 4 - 5 / Inert atmosphere; Reflux 6.1: 1-trans-IODO-4-CYCLOHEXYL / N,N-dimethyl-formamide / 78 h / Reflux; Inert atmosphere View Scheme

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere 1.2: 0.83 h / -78 - 20 °C / Inert atmosphere 1.3: 0 °C / pH 5 - 6 / Inert atmosphere 2.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water / 16 h / 0 °C / pH 4 - 5 / Inert atmosphere; Reflux 4.1: 1-trans-IODO-4-CYCLOHEXYL / N,N-dimethyl-formamide / 78 h / Reflux; Inert atmosphere View Scheme

1.1: potassium carbonate / acetone / 18 h / Reflux 2.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere 2.2: 0.83 h / -78 - 20 °C / Inert atmosphere 2.3: 0 °C / pH 5 - 6 / Inert atmosphere 3.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water / 16 h / 0 °C / pH 4 - 5 / Inert atmosphere; Reflux 5.1: 1-trans-IODO-4-CYCLOHEXYL / N,N-dimethyl-formamide / 78 h / Reflux; Inert atmosphere View Scheme

1.1: thionyl chloride; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Neat (no solvent); Reflux 2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 18 h / Reflux 4.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere 4.2: 0.83 h / -78 - 20 °C / Inert atmosphere 4.3: 0 °C / pH 5 - 6 / Inert atmosphere 5.1: sodium tetrahydroborate / methanol / 0.75 h / 0 - 20 °C / Inert atmosphere 6.1: hydrogenchloride / methanol; water / 16 h / 0 °C / pH 4 - 5 / Inert atmosphere; Reflux 7.1: 1-trans-IODO-4-CYCLOHEXYL / N,N-dimethyl-formamide / 78 h / Reflux; Inert atmosphere View Scheme

hydrogenchloride; sulfuric acid Einleiten von Chlorwasserstoff;

1: aqueous hydrochloric acid; sulfuric acid / 50 °C / Einleiten von Chlorwasserstoff 2: Raney nickel; ethanol / 150 - 200 °C / 25742.8 Torr / Hydrogenation View Scheme

2: tetrahydrofuran; lithium alanate; diethyl ether / -60 °C / anschliessend Behandeln mit wss. Schwefelsaeure und Erhitzen des Reaktionsprodukts mit wss. Salzsaeure View Scheme