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Potassium Hydroxide → 5-Chloro-2-[2-(6-chloro-2-pyridyl)propen-3-yl]-2-methylindan 1,3-dion

HRID 1461633
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1461633
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH3:14])[C:7]2=[O:15].[Cl:16][C:17]1[N:22]=[C:21]([C:23]([CH2:25]Cl)=[CH2:24])[CH:20]=[CH:19][CH:18]=1>CO.[I-].[K+]>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([CH2:25][C:23]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:16])[N:22]=1)=[CH2:24])([CH3:14])[C:7]2=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 150087112-Chloro-6-(3-chloroprop-1-en-2-yl)pyridineHCID 539304495-Chloro-2-methylindan-1,3-dione

Produkt 1

HCID 151168185-Chloro-2-[2-(6-chloro-2-pyridyl)propen-3-yl]-2-methylindan 1,3-dionAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium Iodide
Katalysator
HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 20 ml of methanol was dissolved 1.32 g of 85% potassium hydroxide, and then 3.89 g of 5-chloro-2-methylindan-1,3-dione, 3.76 g of 6-chloro-2-(1-chloromethylvinyl)pyridine and 0.05 g of potassium iodide were added to the solution. After refluxing under heating for 3 hours, the solvent was evaporated and water was poured. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water and with a saturated saline solution, and then dried over anhydrous magnesium sulfate. After the solvent was evaporated, the residue was separated and purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=5/1) to obtain 6.02 g of the compound No. 115 shown in Table 1.

Aufarbeitung

  1. temperatureAfter refluxing
  2. temperatureunder heating for 3 hours
  3. customthe solvent was evaporated
  4. additionwater was poured
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with water and with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter the solvent was evaporated
  9. customthe residue was separated
  10. custompurified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-ede28d899e7843c5873d4f5d0c3499ea
Quelldatensatz
uspto-grants-1991_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05076830

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