sodium hydride in tetrahydrofuran 1 h; Heating;

1.1: Ac2O / 1 h / 140 °C 1.2: 90 percent / ethanol / 20 °C 2.1: K2CO3 / dioxane View Scheme

1.1: Ac2O / 1 h / 140 °C 1.2: 90 percent / ethanol / 20 °C 2.1: K2CO3 / dioxane View Scheme

1: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h 2: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 3: 59.6 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme

1: thionyl chloride / 2 h / 80 °C 2: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h 3: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 4: 59.6 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme

1: 73.2 percent / trifluoroacetic acid, 7.5 N aq. HCl / 24 h / Heating 2: thionyl chloride / 2 h / 80 °C 3: 1.) n-BuLi, biquinoline / 1.) THF, hexane, from -30 deg C to -5 deg C, 2.) THF, hexane, RT, 1 h 4: 1.) Ac2O / 1.) 130 deg C, 1 h, 2.) CH2Cl2, RT, 0.5 h 5: 59.6 percent / NaH / tetrahydrofuran / 1 h / Heating View Scheme

pyridine 3 h; Ambient temperature;

pyridine 3 h; Ambient temperature;

pyridine 3 h; Ambient temperature;