Tetrahydrofuran → HCID 12017933, compound

HRID 1826067Notes

Reaction equation

HRID 1826067 reaction equation
C([C:3](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([N+:18]([O-])=O)[CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])C.[O:21]1CCC[CH2:22]1>[Pd].C(O)C>[NH2:18][C:12]1[CH:11]=[C:10]([CH2:9][CH:3]([O:21][CH3:22])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68849152Ethyl 2-[(4-methoxy-3-nitrophenyl)methylidene]butanoate

Product 1

HCID 12017933HCID 12017933, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Next, ethyl 2-ethyl-3-(4-methoxy-3-nitrophenyl)acrylate (4.50 g, 16.0 mmol), 10% palladium on carbon (1.50 g) and a 1:1 mixed solvent (150 mL) of tetrahydrofuran with ethanol were mixed and hydrogenation was carried out at an initial pressure of 294.3 kPa at room temperature. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford 3.84 g (95%) of the title compound as colorless crystals.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ca44e04dfc714a78ac824bf24b97ca68
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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