Reaktion #81769

Reaktionsgleichung

2,4,6-triiodophenol

potassium carbonate

2-cyclopentylethylmethanesulfonate

→

desired product

Ausbeute 73.0%

2-(2,4,6-Triiodophenoxy)ethylcyclopentane

Ausbeute 73.0%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise over 10 minutes
2. 2
   Sonstigethe solvent was then removed under vacuum
3. 3
   SonstigeThe resulting amber residue was partitioned between ethyl acetate (200 ml) and water (30 ml)
4. 4
   ExtraktionThe aqueous layer was further extracted with ethyl acetate (2×250 ml)
5. 5
   workup.ADDITIONthe combined ethyl acetate extracts were treated with decolorizing carbon
6. 6
   Trocknendried over magnesium sulfate
7. 7
   SonstigeThe filtrate was evaporated under vacuum

Vorschrift

To a stirred mixture of 2,4,6-triiodophenol (20.36 g, 43.2 mmol) and milled anhydrous potassium carbonate (7.2 g, 52.2 mmol) in 75 ml of dry dimethylformamide was added dropwise over 10 minutes, a solution of 2-cyclopentylethylmethanesulfonate (8.2 g, 42.7 mmol) in 10 ml of dimethylformamide. The mixture was heated at 65° C. under argon overnight and the solvent was then removed under vacuum. The resulting amber residue was partitioned between ethyl acetate (200 ml) and water (30 ml). The aqueous layer was further extracted with ethyl acetate (2×250 ml) and the combined ethyl acetate extracts were treated with decolorizing carbon, dried over magnesium sulfate and passed through a short pad of basic alumina. The filtrate was evaporated under vacuum to give 17.5 g (73%) of the desired product as an amber oil.

Quelle