Water → 3-Ethyl-1-phenyl-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin

HRID 34285ノート

反応式

HRID 34285 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([N:10]1[CH2:16][C:15]2([O:23][CH:12]([C:13]3[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=32)[CH2:11]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)[CH3:8].O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:10]1[CH2:16][C:15]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:23][CH:12]([C:13]3[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=32)[CH2:11]1)[CH3:8]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 142087083-Acetyl-1,5-epoxy-1-phenyl-1,2,4,5-tetrahydro-3-benzazepinHCID 21226445Aluminium lithium hydride

生成物 1

HCID 142087093-Ethyl-1-phenyl-1,5-epoxy-1,2,4,5-tetrahydro-3-benzazepin収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of LiAlH4 (910 mg, 23.95 mM) in dry THF (40 ml) under N2 was added the compound from Example 8 (2.22 g, 7.96 mM) in one portion and the resulting mixture refluxed for one hour. The mixture was then cooled in an ice bath and treated successively with distilled water (0.9 ml), 15% NaOH solution (0.9 ml) and water (2.7 ml) in a dropwise manner. The resulting white suspension was filtered through Celite, the filtrate washed thoroughly with THF, and the combined washings concentrated in vacuo. The residue was recrystallized from hexane to give the titled compound (1.89 g, 90% yield) as white crystals, mp 132°-134° C. NMR (CDCl3) δ 0.90 ppm (t, 3H, NCH2CH3), 2.43 (q, 2H, J=7 Hz, NCH2CH3), 2.63 (AB doublet, 1H, J=11 Hz, ##STR19## 2.72 (m, 2H, ##STR20## 3.25 (AB doublet, 1H, J=11 Hz, ##STR21## 5.20 (broad t, 1H, ##STR22## 6.70-7.70 (m, 9H, aromatic H). MS: 265 (M+).

後処理

  1. temperaturethe resulting mixture refluxed for one hour
  2. temperatureThe mixture was then cooled in an ice bath
  3. filtrationThe resulting white suspension was filtered through Celite
  4. washthe filtrate washed thoroughly with THF
  5. concentrationthe combined washings concentrated in vacuo
  6. customThe residue was recrystallized from hexane

出典と根拠

ORDレコード
ord-e01f95e59f6846aa97b2079c097be34a
出典データセット
uspto-grants-1988_08
特許番号
US04761413

反応ノート

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