Potassium Carbonate → 2-(2,4,6-Triiodophenoxy)pentadecane

HRID 53479

Reaktionsgleichung

Reaktionsgleichung von HRID 53479
CS([O:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:7])(=O)=O.[CH:21]1[C:22]([I:30])=[CH:23][C:24]([I:29])=[C:25](O)[C:26]=1[I:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:27][C:26]1[CH:25]=[C:24]([I:29])[CH:23]=[C:22]([I:30])[C:21]=1[O:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:7]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 153433082-Methanesulfonyloxypentadecane

Produkt 1

HCID 153433092-(2,4,6-Triiodophenoxy)pentadecaneAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 2-methanesulfonyloxypentadecane (15.5 g, 48.1 mmol) in dry DMF (200 ml) was added triiodophenol (22.6 g, 47.9 mmol) and potassium carbonate (6.6 g, 47.8 mmol). The reaction flask was immersed in an oil bath which was heated to 85° C. over a period of 0.5 hr. The reaction was stirred under N2 atmosphere for 16 hrs. At the end of this period the reaction was processed as for Example 1 except at 4 times the volumes to provide a brown residue. Flash column chromatography (silica, hexanes) provided 2-(2,4,6-triiodophenoxy)pentadecane (19.2 g, 58.8%) as a white solid. Mp: 56°-58° C.

Aufarbeitung

  1. customThe reaction flask was immersed in an oil bath
  2. customto provide a brown residue

Quellen und Nachweise

ORD-Eintrag
ord-6d086265e8984efb9940057dc09b3172
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620677

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