Ethylene Glycol → HCID 18673916, compound

HRID 1635975Notes

Reaction equation

HRID 1635975 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[CH2:20](O)[CH2:21][OH:22].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1C=CC=CC=1>[CH3:18][C:17]1([C:14]2[CH:15]=[CH:16][C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=3)=[CH:12][CH:13]=2)[O:22][CH2:21][CH2:20][O:19]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 17405231HCID 17405231, compound

Product 1

HCID 18673916HCID 18673916, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

380 mg of 1-{4-[(5-nitro-2-pyridinyl)oxy]phenyl}-1-ethanone was dissolved in 5 ml of benzene and, after adding 98 μl of ethylene glycol and 3 mg of (±)-10-camphorsulfonic acid, the mixture was heated at reflux. After 3 hours, the reaction solution was extracted with ethyl acetate. The organic layer was washed in turn with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: ethyl acetate/n-hexane (1:4)) to obtain the titled compound (280 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed in turn with a saturated sodium hydrogencarbonate solution
  5. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (eluent: ethyl acetate/n-hexane (1:4))

Sources & evidence

ORD record
ord-10197552adcd402ab1d40ce6e08bb0dd
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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