Reaction #51615

Reaction equation

Diethylazodicarboxylate

3-hydroxy-6,7-dimethoxyquinoline

cyclohexanol

Ph3P

→

3-Cyclohexyloxy-6,7-dimethoxyquinoline

Solvents

THF

Conditions

Workup

1. 1
   ConcentrationAfter 4 hours the solution is concentrated
2. 2
   Otherthe residue chromatographed (50% EtOAc in hexanes)
3. 3
   OtherThe product is recrystallized from isopropanol/hexanes as the HCl salt as a white solid (m.p. 229-232° C., dec.)

Procedure

To a THF solution (30 mL) at 0° C. is added 3-hydroxy-6,7-dimethoxyquinoline (0.237 g, 1.15 mmol), cyclohexanol (0.347 g, 3.46 mmol), Ph3P (0.908 g, 3.46 mmol). Diethylazodicarboxylate is added portionwise until the solution retained a deep red color (0.663 g, 3.81 mmol). After 4 hours the solution is concentrated and the residue chromatographed (50% EtOAc in hexanes). The product is recrystallized from isopropanol/hexanes as the HCl salt as a white solid (m.p. 229-232° C., dec.).

Source