methanol; sodium methylate T=20°C; 1 h;

1.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 2.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 3.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 4.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 4.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 5.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 2.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 3.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 3.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 4.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 2.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 2.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 3.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 1.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 2.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: dichloromethane / 16.5 h / 0 - 20 °C 2.1: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 3.1: sodium hydroxide / water / 5 h / |Reflux 4.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 5.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / |Cooling with ice 5.2: 5 h / 20 °C 6.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 7.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 8.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 9.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 9.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 10.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 2.1: sodium hydroxide / water / 5 h / |Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / |Cooling with ice 4.2: 5 h / 20 °C 5.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 6.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 7.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 8.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 8.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 9.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: sodium hydroxide / water / 5 h / |Reflux 2.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 3.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / |Cooling with ice 3.2: 5 h / 20 °C 4.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 5.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 6.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 7.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 7.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 8.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: dichloromethane / 20.5 h / 0 - 20 °C 2.1: bromine; acetic acid / 4 h / 0 - 20 °C 3.1: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 4.1: sodium hydroxide / water / 5 h / |Reflux 5.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 6.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / |Cooling with ice 6.2: 5 h / 20 °C 7.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 8.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 9.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 10.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 10.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 11.1: sodium methylate; methanol / 1 h / 20 °C View Scheme

1.1: bromine; acetic acid / 4 h / 0 - 20 °C 2.1: magnesium sulphate heptahydrate; potassium permanganate / water / 3 h / |Reflux 3.1: sodium hydroxide / water / 5 h / |Reflux 4.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 5.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / |Cooling with ice 5.2: 5 h / 20 °C 6.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 7.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / |Inert atmosphere 8.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C 9.1: morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere; |Darkness 9.2: 0.3 h / 90 - 100 °C / |Inert atmosphere; |Darkness 10.1: sodium methylate; methanol / 1 h / 20 °C View Scheme