1: diethyl ether 2: diluted KOH-solution View Scheme

diethyl ether

potassium hydroxide

water-d2 1.) -78 deg C, THF, 1 h; Yield given. Multistep reaction;

(methylation);

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 20 h / -78 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 20 °C / Inert atmosphere View Scheme

1.) THF, hexane, -78 deg C, 10 min, 2.) a) warm to RT, b) RT, 10 min; Yield given. Multistep reaction;

aluminium trichloride in dichloromethane T=0 - 20°C;

potassium hydroxide in ethanol

1: 1.) lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C -> room temperature 2: 98 percent / potassium carbonate / acetone / 11 h / Heating 3: 1.) lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, DMSO, hexane, 0 deg C, 30 min 4: 98 percent / pyridine / 24 h / Ambient temperature 5: potassium dichromate, glacial acetic acid / 8 h / Ambient temperature 6: 0.160 g / potassium carbonate / methanol / 15 h / Ambient temperature 7: 35 percent / potassium hydroxide / methanol / 14 h / Heating View Scheme