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

HRID 1017873Notes

Reaction equation

HRID 1017873 reaction equation
[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

Participants

6

Reactant 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

Product 1

HCID 10222696N-(4-Methoxybenzyl)-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amineYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-88442c3db7f2443da5855f3cfbb70ef2
Source dataset
uspto-grants-2002_11
Patent number
US06479536B1

Reaction notes

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