Ethanol → HCID 66725896, compound

HRID 1042100Notes

Reaction equation

HRID 1042100 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]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:12]=2)=[CH:6][N:5]=1.[Cl-].[Ca+2].[Cl-].O.C(O)C>[Fe].C(OCC)(=O)C.CCCCCC>[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]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:12]=2)=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 5284359Calcium ChlorideHCID 66726187HCID 66726187, compound

Product 1

HCID 66725896HCID 66725896, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(methoxymethyl)-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine (680 mg), iron powder (530 mg), calcium chloride (20 mg), water (3 mL), and ethanol (15 mL) was heated under reflux for 3 hr. The reaction solution was cooled to room temperature, filtered through celite, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:4, volume ratio) to give the title compound (480 mg, yield 76%) as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hr
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained crude product

Sources & evidence

ORD record
ord-64ca16c54611466289911378fe446e7d
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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