1: With methanesulfonyl chloride; triethylamine in toluene T=0°C; 1 h; 2: With lithium chloride in N,N-dimethyl-formamide T=20°C; 24 h;

1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C / Inert atmosphere 2: tetrachloromethane; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere View Scheme

1: hydrogenchloride; water / tetrahydrofuran / 1.2 h / Inert atmosphere; Reflux 2: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C / Inert atmosphere 3: tetrachloromethane; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride; water / tetrahydrofuran / 1.2 h / Inert atmosphere; Reflux 3.1: sodium tetrahydroborate / methanol / 0.67 h / 0 - 20 °C / Inert atmosphere 4.1: tetrachloromethane; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere View Scheme

Multistep reaction;

1.1: 1,2-dibromoethane; magnesium / tetrahydrofuran / 20 °C 1.2: tetrahydrofuran / 20 h / -78 - 20 °C 2.1: p-toluenesulfonic acid / benzene / 2 h / Heating View Scheme