Barium Sulfate → 3-Acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrile

HRID 361902Notes

Reaction equation

HRID 361902 reaction equation
[C:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:3])[CH3:2].S([O-])([O-])(=O)=O.[Ba+2]>O1CCCC1.C(O)C.[Pd]=O>[C:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]#[N:14])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24414Barium SulfateHCID 54193081HCID 54193081, compound

Product 1

HCID 218444313-Acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrileYield 69.7%

Reagents, catalysts & solvents 3

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1H-NMR (CDCl3) δ: 2.69 (3H, s), 3.85 (3H, s), 6.98 (2H, d, J=10 Hz), 7.50-7.80 (6H, m), 8.36 (1H) d) 7.8 g of 3-acetyl-2-[2-(4-methoxyphenyl)-vinyl]-5-benzofurancarbonitrile obtained in the above step c) was dissolved in a solvent mixture of 600 ml of tetrahydrofuran and 500 ml of ethanol. 900 mg of palladium oxide.1H2O.barium sulfate was added to the above solution, and the mixture was subjected to catalytic hydrogenation under normal pressure for 3.5 hours. After removing the catalyst by filtration, the resulting filtrate was concentrated to dryness. The residue thus obtained was extracted with ethyl acetate, and the resulting organic layer was washed with water, and dried to distill off the solvent. Thereafter, the residue thus obtained was washed with methanol to collect precipitated crystals by filtration, thereby obtaining 5.47 g of 3-acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrile in the form of colorless prism crystals.

Workup

  1. customobtained in the above step c)
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. concentrationthe resulting filtrate was concentrated to dryness
  5. customThe residue thus obtained
  6. extractionwas extracted with ethyl acetate
  7. washthe resulting organic layer was washed with water
  8. customdried
  9. distillationto distill off the solvent
  10. customThereafter, the residue thus obtained
  11. washwas washed with methanol
  12. customto collect
  13. customprecipitated crystals
  14. filtrationby filtration

Sources & evidence

ORD record
ord-22c9d9b8c55849c2ae1ec188ba737abf
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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