2,4,6-Triiodophenol → 2,4,6-Triiodophenyl (2-propyl)pentanoate

HRID 1741995

Reaktionsgleichung

Reaktionsgleichung von HRID 1741995
[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].[CH2:11]([CH:14]([CH2:18][CH2:19]C)[C:15](Cl)=[O:16])[CH2:12][CH3:13].[C:21](=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:21][CH:18]([CH:14]([CH2:11][CH2:12][CH3:13])[C:15]([O:10][C:3]1[C:2]([I:1])=[CH:7][C:6]([I:8])=[CH:5][C:4]=1[I:9])=[O:16])[CH3:19]

Komponenten

6

Edukt 3

HCID 118622,4,6-TriiodophenolHCID 762402-Propylvaleryl chlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 867478922,4,6-Triiodophenyl (2-propyl)pentanoateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2,4,6-triiodophenol (2.0 g, 4.24 mmol), 2-propylvaleroyl chloride (2.5 ml, 12.7 mmol, 3 eq) and 4-dimethylaminopyridine (DMAP; 20 mg) in 20 ml of acetonitrile was refluxed under argon overnite. The reaction mixture was cooled and poured into excess aqueous sodium bicarbonate and then extracted with dichloromethane. The dichloromethane extract was dried over magnesium sulfate, filtered, and evaporated to give the crude product (2.42 mmol, 95%) as a pink solid. Recrystallization from ethyl acetate gave 1.75 g (68%) of pure product, mp 99°-101° C.

Aufarbeitung

  1. temperaturewas refluxed under argon overnite
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. extractionThe dichloromethane extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product (2.42 mmol, 95%) as a pink solid
  9. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1d8b5c1a325a4bee9e58a464aa9e8eda
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05336484

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