Hexane → HCID 66726077, compound

HRID 1042111Notes

Reaction equation

HRID 1042111 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23][CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:15]=2)=[CH:9][N:8]=1.[Cl-].[Ca+2].[Cl-].C(OCC)(=O)C.CCCCCC>C(O)C.O.[Fe]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[N:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([O:23][CH:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[CH:15]=2)=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 5284359Calcium ChlorideHCID 66725952HCID 66725952, compound

Product 1

HCID 66726077HCID 66726077, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-[(2-methoxyethoxy)methyl]-5-[4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenoxy]pyridine (11.5 g) in ethanol (100 mL) and water (25 mL) were added iron powder (8 g) and calcium chloride (0.3 g), and the mixture was stirred with heating under reflux for 4 hr. The reaction mixture was cooled, and insoluble material was filtered off through celite. Water was added to the filtrate, 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 (ethyl acetate:hexane=0:100 to 50:50, volume ratio) to give the title compound (7.84 g, yield 74%) as an orange oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationinsoluble material was filtered off through celite
  5. additionWater was added to the filtrate
  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-bbd80228d75c44dda0a4e0bb031970a7
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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