Hydrochloric Acid → Benzeneethanol, beta-((5-(hexyloxy)-1H-indol-2-yl)thio)-beta-methyl-

HRID 846675노트

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HRID 846675 반응식
[CH2:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([S:17][C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[C:19](O)=[O:20])=[CH:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH2:1]([O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([S:17][C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH2:19][OH:20])=[CH:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 157249712-(5-hexyloxy-1H-indol-2-yl)thio-2-phenylpropionic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 3076999Benzeneethanol, beta-((5-(hexyloxy)-1H-indol-2-yl)thio)-beta-methyl-수율 61.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution (20 ml) of 2-(5-hexyloxy-1H-indol-2-yl)thio-2-phenylpropionic acid (2.81 g) in anhydrous tetrahydrofuran was added dropwise to a suspension (10 ml) of lithium aluminum hydride (0.4 g) in anhydrous tetrahydrofuran, and the mixture was heated and refluxed for 30 minutes. The reaction solution was allowed to cool, and was poured into ice water. The mixture was acidified by adding 6N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, and a saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was crystallized by adding n-hexane. The crude crystalline matter was recrystallized from ethanol to give 1.66 g (yield: 61 %) of the product compound as a pale green prism crystal. The melting point was 93.5°-95.5° C.

후처리

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 30 minutes
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was crystallized
  9. additionby adding n-hexane
  10. customThe crude crystalline matter was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-badf78d46a674d2092f9fba55d5c2db3
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05137909

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