HCID 42643743, compound → HCID 12770688, compound

HRID 474707Notes

Reaction equation

HRID 474707 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](=O)[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])([O-])=O>CC(O)=O.[Fe]>[NH:1]1[C:4]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:10]=[C:11]1[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 1

HCID 42643743HCID 42643743, compound

Product 1

HCID 12770688HCID 12770688, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

The mixture of Methyl 5-(2-nitrophenyl)-4-oxopentanoate (4.29 g, 17.08 mmol) and Iron powder (6.0 g, 107 mmol) in AcOH (75 mL) was heated at reflux for 3 h. The crude mixture was concentrated under reduced pressure and diluted with ethyl acetate. The organic solution was washed with NaOH solution, brine, sodium sulfate, filtered, and concentrated. Purification via flash chromatography then afforded the title compound (3.1 g, 14.49 mmol, 85% yield). LCMS: rt=2.86 min, [M+H+]=204.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationThe crude mixture was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washThe organic solution was washed with NaOH solution, brine, sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-a2cc8556925e4c9ab65151fe1a2d24e5
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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