Sodium Hydroxide → N-(4-Methoxybenzyl)-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amine

HRID 2211754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2211754
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][O:12][C:13]1[CH:41]=[CH:40][C:16]([C:17]([NH:19][C:20]2[C:21]([CH3:39])=[C:22]([CH3:38])[C:23]3[O:27][C:26]([CH3:29])([CH3:28])[CH:25]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]=3[C:36]=2[CH3:37])=O)=[CH:15][CH:14]=1.[OH-].[Na+]>O1CCCC1>[CH3:11][O:12][C:13]1[CH:41]=[CH:40][C:16]([CH2:17][NH:19][C:20]2[C:21]([CH3:39])=[C:22]([CH3:38])[C:23]3[O:27][C:26]([CH3:29])([CH3:28])[CH:25]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:24]=3[C:36]=2[CH3:37])=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 101801024-Methoxy-N-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)benzamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10222696N-(4-Methoxybenzyl)-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amineAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of aluminum chloride (2.25 g, 16.9 mmol) in tetrahydrofuran (20 ml) was gradually added under ice cooling lithium aluminum hydride (640 mg, 16.9 mmol) and the resulting mixture was stirred at the same temperature for 10 minutes. To this mixture was added 4-Methoxy-N-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)benzamide (1.40 g, 3.37 mmol) and the mixture was refluxed with heating for 3 hours. The reaction mixture was poured into ice water and neutralized with an 8 N aqueous solution of sodium hydroxide. The product was extracted twice with ethyl acetate. The combined organic layers were washed with water, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from methanol to obtain 0.80 g (59% yield) of the title compound. Melting point: 113-115° C.

Aufarbeitung

  1. additionwas gradually added under ice
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 3 hours
  4. extractionThe product was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. customdried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-dec0ca73422a441c97c01e29359837e8
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101867B2

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