Potassium Carbonate → 2-Ethyl-1-(2,4,6-triiodophenoxy)-hexane

HRID 1733762

Reaktionsgleichung

Reaktionsgleichung von HRID 1733762
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4]Br)[CH3:2].[CH:10]1[C:11]([I:19])=[CH:12][C:13]([I:18])=[C:14]([OH:17])[C:15]=1[I:16].C(=O)([O-])[O-].[K+].[K+].IC1C=C(I)C=C(I)C=1OC(CC)C>CN(C=O)C>[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][O:17][C:14]1[C:15]([I:16])=[CH:10][C:11]([I:19])=[CH:12][C:13]=1[I:18])[CH3:2]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 868042-Ethylhexyl bromideHCID 158141292-(2,4,6-Triiodophenoxy)butane

Produkt 1

HCID 153433142-Ethyl-1-(2,4,6-triiodophenoxy)-hexaneAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2-Ethyl-bromohexane (10.4 g, 53.0 mmol), triiodophenol (25.5 g, 54.0 mmol) and potassium carbonate (7.5 g, 54.3 mmol) were reacted in dry DMF (110 ml) at 77° C. as for 2-(2,4,6-triiodophenoxy)butane. After stirring for 20 hrs, the reaction was cooled, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up in EtOAc (500 ml), washed with water (200 ml), 1N aqueous sodium hydroxide (200 ml), water (2×200 ml) and brine (200 ml), dried (Na2SO4), filtered and evaporated. Flash column chromatography (silica, hexanes) provided 2-ethyl-1-(2,4,6-triiodophenoxy)-hexane (22.8 g, 73.7%) as a clear viscous oil.

Aufarbeitung

  1. temperaturethe reaction was cooled
  2. filtrationfiltered through a pad of celite
  3. customevaporated in vacuo
  4. washwashed with water (200 ml), 1N aqueous sodium hydroxide (200 ml), water (2×200 ml) and brine (200 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-75482432e30b42fcaa280512f48fdeab
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05531979

Verknüpfte Notizen

Wird geladen…