Reaktion #81771

Reaktionsgleichung

potassium carbonate

geranyl bromide

water

triiodophenol

→

(E)-1-(2,4,6-Triiodophenoxy)-3,7-dimethyl-2,6-octadiene

Ausbeute 87.0%

Lösungsmittel

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   ExtraktionThe ethyl acetate extract
4. 4
   Filtrationwas filtered through a short pad of silica gel
5. 5
   Waschenalumina, eluting with ethyl acetate-hexanes (1:1)
6. 6
   EinengenThe eluent was concentrated under high vacuum
7. 7
   Sonstigeto give the product in 87% yield as an oil

Vorschrift

A mixture of triiodophenol (10.0 g, 21.2 mmol), milled potassium carbonate (3.1 g, 22.5 mmol, 1.06 eq) and geranyl bromide (4.0 ml, 20.2 mmol) in dimethyl formamide (25 ml) was heated to 50° C. for 2 hrs and cooled. The mixture was poured into 300 ml of water and extracted with ethyl acetate. The ethyl acetate extract was filtered through a short pad of silica gel, then alumina, eluting with ethyl acetate-hexanes (1:1). The eluent was concentrated under high vacuum to give the product in 87% yield as an oil.

Quelle