Reacción #81770

Ecuación de reacción

2,4,6-triiodophenol

potassium carbonate

citronellol

triethylamine

methanesulfonyl chloride

→

desired product

Rendimiento 15.0%

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

Rendimiento 15.0%

Disolventes

water

dimethylformamide

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   SecadoThe dichloromethane layer was dried over magnesium sulfate
3. 3
   Lavadoafter washing with saturated aqueous sodium chloride
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   Otroto give an oil
6. 6
   TemperaturaThe mixture was heated to 100° C. for 30 minutes
7. 7
   Temperaturacooled to room temperature
8. 8
   OtroThe crude product was isolated
9. 9
   Otroby partitioning the reaction mixture between water and dichloromethane
10. 10
    ConcentraciónThe organic layer was concentrated under vacuum
11. 11
    Otroto give an oil
12. 12
    OtroThe oil was purified

Procedimiento

To a stirred solution of citronellol (4.5 g, 28.8 mmol) and triethylamine (5.2 ml, 34.6 retool, 1.2 eq) in dichloromethane (50 ml) cooled to 0° C. was added dropwise, a solution of methanesulfonyl chloride (2.46 ml, 28.8 mmol) in dichloromethane (50 ml). The solution was stirred for 1 hr at 0° C. under nitrogen and then water was added. The dichloromethane layer was dried over magnesium sulfate after washing with saturated aqueous sodium chloride and then concentrated in vacuo to give an oil. 1H-NMR (300 MHZ) spectrum of the oil indicated the desired methanesulfonate ester. The methanesulfonate ester was added to a stirred mixture of 2,4,6-triiodophenol (13.6 g, 28.8 mmol) and potassium carbonate (4.0 g, 28.8 mmol) in dimethylformamide (50 ml). The mixture was heated to 100° C. for 30 minutes and cooled to room temperature. The crude product was isolated by partitioning the reaction mixture between water and dichloromethane. The organic layer was concentrated under vacuum to give an oil. The oil was purified by flashing through basic alumina with hexanes to give the desired product in 15% yield as a light-sensitive oil.

Fuente