Water → 6-Iodohexyl-(4,4,5,5,5-pentafluoropentyl)malonic acid diethyl ester

HRID 1792423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792423
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Cl)([CH2:11][CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[I-:29].[Na+].O>CC(C)=O>[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][I:29])([CH2:11][CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5238Sodium IodideHCID 867601656-Chlorohexyl-(4,4,5,5,5-pentafluoropentyl)malonic acid diethyl ester

Produkt 1

HCID 867601666-Iodohexyl-(4,4,5,5,5-pentafluoropentyl)malonic acid diethyl esterAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 6-chlorohexyl-(4,4,5,5,5-pentafluoropentyl)malonic acid diethyl ester (743 mg, 1.69 mmol) in acetone (5 ml) was added sodium iodide (761 mg, 5.08 mmol), which was then refluxed for 4 h. When the reaction was completed, water was added to the reaction mixture and extracted with ethyl acetate. Then, the organic layer was washed with wafer and saturated sodium chloride solution. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=15:1) to give the title compound (801 mg, yield: 89%) as a colorless liquid.

Aufarbeitung

  1. temperaturewas then refluxed for 4 h
  2. extractionextracted with ethyl acetate
  3. washThen, the organic layer was washed with wafer and saturated sodium chloride solution
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7d17d3645d6548c9873294a02e062c24
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074819B2

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