potassium hydroxide in ethanol

1: trifluoroacetic acid 2: oxalyl chloride / CH2Cl2 3: pyridine / CH2Cl2 4: Heating 5: aq. NaOH / tetrahydrofuran View Scheme

1: oxalyl chloride / CH2Cl2 2: pyridine / CH2Cl2 3: Heating 4: aq. NaOH / tetrahydrofuran View Scheme

1: pyridine / CH2Cl2 2: Heating 3: aq. NaOH / tetrahydrofuran View Scheme

1.1: tetrahydrofuran / 2 h / Cooling 1.2: 1 h / Reflux 2.1: tetrahydrofuran / 1 h / Reflux 3.1: N-bromosuccinmide / dichloromethane / 3 h / Reflux 4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.05 h / -60 °C 4.2: 0.25 h / -60 °C 5.1: lithium hexamethyldisilazane / tetrahydrofuran / -60 - 20 °C 6.1: water; acetic acid / tetrahydrofuran / 0.5 h / 50 °C 7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -48 °C 7.2: -48 - 20 °C 7.3: 0.5 h / 20 °C View Scheme

1.1: tetrahydrofuran / 1 h / Reflux 2.1: N-bromosuccinmide / dichloromethane / 3 h / Reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.05 h / -60 °C 3.2: 0.25 h / -60 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / -60 - 20 °C 5.1: water; acetic acid / tetrahydrofuran / 0.5 h / 50 °C 6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -48 °C 6.2: -48 - 20 °C 6.3: 0.5 h / 20 °C View Scheme

1.1: N-bromosuccinmide / dichloromethane / 3 h / Reflux 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.05 h / -60 °C 2.2: 0.25 h / -60 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / -60 - 20 °C 4.1: water; acetic acid / tetrahydrofuran / 0.5 h / 50 °C 5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -48 °C 5.2: -48 - 20 °C 5.3: 0.5 h / 20 °C View Scheme

sodium hydroxide in tetrahydrofuran

sodium hydroxide in tetrahydrofuran

1: 78 percent / Et3N, N,N'-dicyclohexylcarbodiimide / CH2Cl2 2: 60 percent / sodium methoxide / tetrahydrofuran 3: 53 percent / KOH / ethanol View Scheme