Phenoxazine → HCID 59221271, compound

HRID 424344Notes

Reaction equation

HRID 424344 reaction equation
C([Li])CCC.[CH:6]1[C:19]2[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.Br[CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27]>C1COCC1>[CH3:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][N:18]1[C:19]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:11][C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2

Participants

5

Reactant 3

HCID 67278PhenoxazineHCID 1235321-Bromo-3,6-dioxaheptaneHCID 178418339Butyllithium

Product 1

HCID 59221271HCID 59221271, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customstirring for 1 h
  2. stirringstirred overnight
  3. customafter which the resultant dark orange solution was quenched with water
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. distillationThe crude mixture was purified by chromatography and Kugelrohr distillation

Sources & evidence

ORD record
ord-f17fe54c673c4dc58b39312fb8bd9ae1
Source dataset
uspto-grants-2012_01
Patent number
US08105865B2

Reaction notes

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