1: 85.6 percent / phosphorus oxychloride / 3 h / Heating 2: 95.5 percent / powdered zinc / acetic acid / 5 h / Heating View Scheme

potassium fluoride in methanol

1: water; sodium hydroxide / tetrahydrofuran / 15 h / Reflux; Inert atmosphere 2: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 3: sodium periodate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere 4: diisobutylaluminium hydride / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 5: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 10 h / Reflux; Inert atmosphere 2: water; sodium hydroxide / tetrahydrofuran / 15 h / Reflux; Inert atmosphere 3: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 4: sodium periodate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere 5: diisobutylaluminium hydride / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 6: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere View Scheme

1: diisobutylaluminium hydride / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere View Scheme

1: chloroform / 10 h / Reflux; Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 10 h / Reflux; Inert atmosphere 3: water; sodium hydroxide / tetrahydrofuran / 15 h / Reflux; Inert atmosphere 4: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 5: sodium periodate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere 6: diisobutylaluminium hydride / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 7: potassium tert-butylate / tetrahydrofuran / 1 h / Reflux; Inert atmosphere View Scheme

T=90°C; 1 h;

methyl lithium LiBr complex; water 1.) THF, ether, -75 deg C, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

1: furolt;2,3-cgt;pyridine With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 2: formic acid ethyl ester in tetrahydrofuran

Yield given. Multistep reaction;