Réaction #81771

Équation de réaction

potassium carbonate

geranyl bromide

water

triiodophenol

→

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

Rendement 87.0%

Solvants

dimethyl formamide

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Extractionextracted with ethyl acetate
3. 3
   ExtractionThe ethyl acetate extract
4. 4
   Filtrationwas filtered through a short pad of silica gel
5. 5
   Lavagealumina, eluting with ethyl acetate-hexanes (1:1)
6. 6
   ConcentrationThe eluent was concentrated under high vacuum
7. 7
   Autreto give the product in 87% yield as an oil

Mode opératoire

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.

Source