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

HRID 846675ノート

反応式

HRID 846675 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-badf78d46a674d2092f9fba55d5c2db3
出典データセット
uspto-grants-1992_08
特許番号
US05137909

反応ノート

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