lithium aluminium tetrahydride in tetrahydrofuran 10 h; Reflux;

in tetrahydrofuran

1: With lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 3 h; Heating / reflux; 2: With hydrogenchloride; water in tetrahydrofuran T=20°C;

1.1: triethylamine / dichloromethane / 0.08 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide; 1-Fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate / Pd(OTf)2 dihydrate / 1,2-dichloro-ethane / 2 h / 120 °C 3.1: potassium carbonate / acetone / 8 h / 20 °C / Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 10 h / 0 °C / Inert atmosphere; Reflux View Scheme

1: N,N-dimethyl-formamide; 1-Fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate / Pd(OTf)2 dihydrate / 1,2-dichloro-ethane / 2 h / 120 °C 2: potassium carbonate / acetone / 8 h / 20 °C / Reflux 3: lithium aluminium tetrahydride / tetrahydrofuran / 10 h / 0 °C / Inert atmosphere; Reflux View Scheme

1: in ethanol Cooling with iceHeating; 2: With hydrogenchloride in water 3: With sodium hydroxide in water pH=9;

1: potassium carbonate / acetone / 8 h / 20 °C / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 10 h / 0 °C / Inert atmosphere; Reflux View Scheme

titanium(IV) isopropylate; sodium tetrahydroborate; triethylamine 1.) EtOH, 25 deg C, 8 h, 2.) EtOH, 25 deg C, 7 h; Yield given. Multistep reaction;