HCID 42643743, compound → HCID 12770688, compound

HRID 705945Notes

Reaction equation

HRID 705945 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-6b3140a724de4cb8a71b209157cbc926
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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