sodium hydroxide

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: 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: 91 percent / tetrahydrofuran / 48 h / 60 °C View Scheme

ethyl mercaptan sodium salt in N,N-dimethyl-formamide T=80°C; 3.5 h;

tri-tert-butyl phosphine; potassium carbonate; acetone; [Rh(C2H4)2Cl]2 in 1,4-dioxane; toluene T=20 - 80°C;

sodium hydride in N,N-dimethyl-formamide; paraffin 1.) rt, 20 min; 50 deg C, 50 min; 2.) rt, overnight;

Envirocat ERICR 0.133333 h; Heating;

methanesulfonic acid; trifluoromethanesulfonic anhydride T=65°C; Fries rearrangement; Inert atmosphere; regioselective reaction;

potassium hydroxide in water; dimethyl sulfoxide T=60°C; 18 h;

potassium hydroxide T=20 - 100°C; 1 h;