1: 4-(1-(4-hydroxylphenyl)-2-phenylbut-1-enyl)phenol With caesium carbonate in N,N-dimethyl-formamide 0.5 h; Reflux; 2: 2-dimethylamino-1-chloro-ethane hydrochloride in N,N-dimethyl-formamide T=120°C; 7 h;

in tetrahydrofuran T=60°C; 43 h;

1.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C 1.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C 2.1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 3.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 4.1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 5.1: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme

1.1: sodium hydride / dimethylformamide / 1 h / 0 °C 1.2: 95 percent / dimethylformamide / 2 h / 20 °C 2.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C 2.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C 3.1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 4.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 5.1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 6.1: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme

1.1: potassium tert-butoxide; n-butyllithium; tetramethylethylenediamine / hexane; tetrahydrofuran / 0.5 h / 20 °C 1.2: 97 percent / hexane; tetrahydrofuran / 4.5 h / -78 - 20 °C 2.1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 3.1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 4.1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 5.1: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme

1: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 2: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 3: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme

1: 93 percent / aq. hydrochloric acid / ethanol; CH2Cl2 / Heating 2: 90 percent / aq. sodium hydroxide; tetrabutylammonium hydrogen sulfate / 18 h / 20 °C 3: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 4: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme

1: 57 percent / boron tribromide / CH2Cl2 / 4.5 h 2: 31 percent / tetrahydrofuran / 43 h / 60 °C View Scheme

1.1: titanium tetrachloride; zinc / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere; Reflux; Darkness 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h / 70 - 80 °C 2.2: 1.75 h View Scheme

1.1: zinc; titanium tetrachloride / tetrahydrofuran / 12 h / -20 °C / |Inert atmosphere; |Reflux; |Darkness 2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / |Reflux 2.2: 7 h / 120 °C View Scheme