Phenoxazine → HCID 59221271, compound

Participants

Reaction Steps

Butyllithium (1.6 M in hexane, 5 ml) was added dropwise to a stirring solution of 10H-phenoxazine (1.00 g, 5.46 mmol) in THF at −78° C. and continued the stirring for 1 h. To this mixture added 1-bromo-2(2-methoxyethoxy)ethane (1.5 ml, 11 mmol) dropwise and stirring continued for another 1 h at −78° C. The mixture was allowed to warm to RT and stirred overnight, after which the resultant dark orange solution was quenched with water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate and evaporated under reduced pressure. The crude mixture was purified by chromatography and Kugelrohr distillation to give the product as a pale yellow oil (1.11 g, 72%). Cyclic voltammetry of MEEP in a 0.1 M tetra-n-butylammonium hexafluorophosphate (TBAPF6) in acetonitrile solution shows a reversible redox couple at 0.26 V vs Fc+/Fc.

Provenance & Evidence