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

HRID 1884252

반응식

HRID 1884252 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7489f92746fb4d7ba0cec264447c0196
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762321B2

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