Reacción #81771

Ecuación de reacción

potassium carbonate

geranyl bromide

water

triiodophenol

→

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

Rendimiento 87.0%

Disolventes

dimethyl formamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   Extracciónextracted with ethyl acetate
3. 3
   ExtracciónThe ethyl acetate extract
4. 4
   Filtraciónwas filtered through a short pad of silica gel
5. 5
   Lavadoalumina, eluting with ethyl acetate-hexanes (1:1)
6. 6
   ConcentraciónThe eluent was concentrated under high vacuum
7. 7
   Otroto give the product in 87% yield as an oil

Procedimiento

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.

Fuente