potassium hydroxide in methanol; water T=80 - 85°C; 2 h;

aluminum oxide T=60°C; 3 h;

1: 65 percent / TMG / acetonitrile / Ambient temperature 2: Bu3SnH, AIBN / toluene / 0.5 h / Heating View Scheme

T=170°C;

1.1: sodium hydride; 15-crown-5 / tetrahydrofuran; mineral oil / 0 °C 1.2: -40 - 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / |Inert atmosphere 3.1: phosphorus tribromide / diethyl ether / 0 °C / |Inert atmosphere 4.1: sodium ethanolate / ethanol / 0 °C 4.2: 16 h / 0 - 20 °C 5.1: potassium hydroxide / methanol; water / 2 h / 80 - 85 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / |Inert atmosphere 2.1: phosphorus tribromide / diethyl ether / 0 °C / |Inert atmosphere 3.1: sodium ethanolate / ethanol / 0 °C 3.2: 16 h / 0 - 20 °C 4.1: potassium hydroxide / methanol; water / 2 h / 80 - 85 °C View Scheme

1.1: phosphorus tribromide / diethyl ether / 0 °C / |Inert atmosphere 2.1: sodium ethanolate / ethanol / 0 °C 2.2: 16 h / 0 - 20 °C 3.1: potassium hydroxide / methanol; water / 2 h / 80 - 85 °C View Scheme

potassium hydroxide; ethanol; NaCH(CO2Et)COCH3 anschl. mit konz. wss. HCl;

1: concentrated aqueous hydrochloric acid 2: sodium-compound of acetoacetic acid ethyl ester; KOH; ethanol / anschl. mit konz. wss. HCl View Scheme

(i), (ii) aq. NaOH; Multistep reaction;