Ethanol → HCID 67118885, compound

HRID 1188940Notes

Reaction equation

HRID 1188940 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([O:20][CH:21]([CH3:23])[CH3:22])[CH:12]=2)=[CH:6][N:5]=1.[Cl-].[Ca+2].[Cl-].C(O)C>[Fe].O>[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([O:20][CH:21]([CH3:23])[CH3:22])[CH:12]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 66885726HCID 66885726, compound

Product 1

HCID 67118885HCID 67118885, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(methoxymethyl)-5-[3-(1-methylethoxy)-4-nitrophenoxy]pyridine (20.5 g), iron (powder, 17.9 g), calcium chloride (710 mg), ethanol (400 mL) and water (100 mL) was refluxed for 5 h. The mixture was filtered with celite. The filtrate was concentrated in vacuo to remove ethanol. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by basic silica gel chromatography (ethyl acetate:hexane=5:95 to 1:3, volume ratio) to give the title compound (13.77 g, 74%) as a brown oil. MS 289 (MH+).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationThe mixture was filtered with celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto remove ethanol
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by basic silica gel chromatography (ethyl acetate:hexane=5:95 to 1:3, volume ratio)

Sources & evidence

ORD record
ord-dc5d12713e514495845d8e8823b43f01
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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