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Phenylsuccinic Anhydride → 1-(2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-3-phenylpyrrolidine-2,5-dione

HRID 1272331
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1272331
[CH3:1][C:2]1([CH3:22])[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[C:5]2[C:14]([CH3:21])=[C:15]([NH2:20])[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]=2[O:3]1.[C:23]1([CH:29]2[CH2:34][C:33](=O)[O:32][C:30]2=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1.C(OC(=O)C)(=O)C>[CH3:1][C:2]1([CH3:22])[CH:6]([C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[C:5]2[C:14]([CH3:21])=[C:15]([N:20]3[C:33](=[O:32])[CH2:34][CH:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:30]3=[O:31])[C:16]([CH3:19])=[C:17]([CH3:18])[C:4]=2[O:3]1
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Komponenten

6

Edukt 3

HCID 136911Phenylsuccinic AnhydrideHCID 517045Sodium AcetateHCID 106853092,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine

Produkt 1

HCID 102044451-(2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-3-phenylpyrrolidine-2,5-dioneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140
Toluene
Lösungsmittel
HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A solution of 2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine (2.95 g, 10 mmol) and phenylsuccinic anhydride (1.94 g, 11 mmol) in toluene was refluxed for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. A mixture of the residue and sodium acetate (0.86 g, 10.5 mmol) in acetic anhydride (60 ml) was stirred at 90° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and removed under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate−4/1) to obtain 2.27 g (yield 50%) of the title compound. mp. 130–131° C. low polarity product, 1H-NMR (CDCl3) δ: 1.00 (3H, s)=1.52 (3H, s), 1.64 (3H, s), 2.02 (3H, s), 2.16 (3H, s), 2.30 (3H, s), 3.00 (1H, dd, J=4.7, 18.5 Hz), 3.36 (1H, dd, J=9.5, 18.5 Hz), 4.15–4.25 (2H, m), 6.85 (2H, br), 7.06 (2H, brd, J=6.6 Hz), 7.30–7.47 (5H, m).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. additionThe residue was diluted with water
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with saturated aqueous sodium chloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. customremoved under reduced pressure
  13. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate−4/1)

Quellen und Nachweise

ORD-Eintrag
ord-ae528176bf5b40a1b00e3b09882a68dd
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07208495B2

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