Sodium Hydroxide → Phenethylamine, 4-(benzyloxy)-3-methoxy-

HRID 1884252

反応式

HRID 1884252 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][N+:23]([O-])=O)=[CH:17][C:16]=1[O:26][CH3:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[CH3:27][O:26][C:16]1[CH:17]=[C:18]([CH2:21][CH2:22][NH2:23])[CH:19]=[CH:20][C:15]=1[O:14][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 158282-Methoxy-4-(2-nitroethenyl)-1-(phenylmethoxy)benzeneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 200382Phenethylamine, 4-(benzyloxy)-3-methoxy-収率 89.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

6.78 g (178.8 mmol) of lithium aluminum hydride and 200 ml of anhydrous tetrahydrofuran were mixed and an anhydrous tetrahydrofuran solution of 17.0 g (59.6 mmol) of 1-benzyloxy-2-methoxy-4-(2-nitrovinyl)benzene was added dropwise thereto over about 90 minutes under vigorous stirring. The mixture was refluxed for 2 hours by heating, and then cooled and aqueous sodium hydroxide solution was added to the mixture. The precipitates were filtered off with celite-precoated glass filter and the solvent was distilled off from the filtrate under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated brine, dried over potassium carbonate and the solvent was distilled off under reduced pressure to give 13.67 g of crude 2-(3-methoxy-4-benzyloxyphenyl)ethylamine.

後処理

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureby heating
  3. temperaturecooled
  4. filtrationThe precipitates were filtered off with celite-precoated glass
  5. filtrationfilter
  6. distillationthe solvent was distilled off from the filtrate under reduced pressure
  7. extractionThe residue was extracted with ethyl acetate
  8. washwashed with saturated brine
  9. dry with materialdried over potassium carbonate
  10. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-7489f92746fb4d7ba0cec264447c0196
出典データセット
uspto-grants-2004_07
特許番号
US06762321B2

関連ノート

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