Ethyl Acetate → HCID 9964543, compound

HRID 901829Notes

Reaction equation

HRID 901829 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13]C)=[O:11])=[C:6](OCC)[CH:5]=1)([O-])=O.[Mg].[C:21](OCC)(=[O:23])[CH3:22]>CO>[CH2:21]([O:23][CH:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:16][CH:15]=1)[C:10]([O:12][CH3:13])=[O:11])[CH3:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5462224MagnesiumHCID 67190505HCID 67190505, compound

Product 1

HCID 9964543HCID 9964543, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-nitro2-ethoxycinnamate (10 g, 1 eq, 37.7 mmol) obtained in step (i) of preparation 1, was treated with activated magnesium turnings (18 g, 20 eq, 754 mmol) in dry methanol (400 ml). The reaction mixture was refluxed for 2-3 h, and allowed to stir at room temperature for 16 h. The reaction mixture was diluted with ethyl acetate and quenched with cold aqueous ammonium chloride. The organic layer was washed with water and brine. The residue was chromatographed using ethyl acetate and hexane to afford the title compound as liquid (6 g, yield 72%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2-3 h
  2. customquenched with cold aqueous ammonium chloride
  3. washThe organic layer was washed with water and brine
  4. customThe residue was chromatographed

Sources & evidence

ORD record
ord-7cd63de7e2f94deca22bf5450783dba6
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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