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Potassium Iodide → Ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyrate

HRID 33603
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 33603
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([OH:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][S:35][C:36]1[CH:41]=[CH:40][C:39]([C:42](=[O:44])[CH3:43])=[C:38]([OH:45])[C:37]=1[CH2:46][CH2:47][CH3:48]>CC(C)=O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([O:22][CH2:32][CH2:33][CH2:34][S:35][C:36]2[CH:41]=[CH:40][C:39]([C:42](=[O:44])[CH3:43])=[C:38]([OH:45])[C:37]=2[CH2:46][CH2:47][CH3:48])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 15623024Ethyl 4-(6-acetyl-3-hydroxy-2-propylphenoxy)butanoateHCID 157123831-{4-[(3-Bromopropyl)sulfanyl]-2-hydroxy-3-propylphenyl}ethan-1-one

Produkt 1

HCID 15712389Ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenylthio)propoxy]-2-propylphenoxy]butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of ethyl 4-(6-acetyl-3-hydroxy-2-propylphenoxy)butyrate (1.6 g), potassium iodide (0.5 g) and potassium carbonate (1.45 g) in acetone (30 ml) was added drop wise a solution of 4-(3-bromopropylthio)-2-hydroxy-3-propylphenyl -ethanone (1.9 g) in acetone (10 ml) with heating to reflux. After refluxing six hours the mixture was cooled to room temperature and inorganic materials were separated by filtration. The filtrate was concentrated and the residue was separated and purified by silica-gel column chromatography (eluting with benzene:ethyl acetate=9:1) to give the title compound as crude crystals (2.1 g, 72.4%) which were recrystallized from ethanol to give colorless crystals, mp 65-66° C.

Aufarbeitung

  1. temperaturewith heating to reflux
  2. temperatureAfter refluxing six hours the mixture
  3. custominorganic materials were separated by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe residue was separated
  6. custompurified by silica-gel column chromatography (eluting with benzene:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-e4d34cbb624d4416a4e5ea2bd09afc16
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07429617B2

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