lithium hydroxide in N,N-dimethyl-formamide T=85°C; 10 h;

potassium hydroxide in methanol 14 h; Heating;

1: 33 percent / diethyl ether 2: 37 percent / LiOH / dimethylformamide / 10 h / 85 °C View Scheme

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

1: 98 percent / pyridine / 24 h / Ambient temperature 2: potassium dichromate, glacial acetic acid / 8 h / Ambient temperature 3: 0.160 g / potassium carbonate / methanol / 15 h / Ambient temperature 4: 35 percent / potassium hydroxide / methanol / 14 h / Heating View Scheme

1: potassium dichromate, glacial acetic acid / 8 h / Ambient temperature 2: 0.160 g / potassium carbonate / methanol / 15 h / Ambient temperature 3: 35 percent / potassium hydroxide / methanol / 14 h / Heating View Scheme

1: 0.160 g / potassium carbonate / methanol / 15 h / Ambient temperature 2: 35 percent / potassium hydroxide / methanol / 14 h / Heating View Scheme

1: 56 percent / 22 h / 160 °C 2: 20 percent / 160 °C 3: 79 percent / BCl3 / CH2Cl2 / 0.13 h / -80 °C 4: 37 percent / LiOH / dimethylformamide / 10 h / 85 °C View Scheme

1: 79 percent / BCl3 / CH2Cl2 / 0.13 h / -80 °C 2: 37 percent / LiOH / dimethylformamide / 10 h / 85 °C View Scheme

1: 20 percent / 160 °C 2: 79 percent / BCl3 / CH2Cl2 / 0.13 h / -80 °C 3: 37 percent / LiOH / dimethylformamide / 10 h / 85 °C View Scheme