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

HRID 1017873ノート

反応式

HRID 1017873 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88442c3db7f2443da5855f3cfbb70ef2
出典データセット
uspto-grants-2002_11
特許番号
US06479536B1

反応ノート

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