Reaktion #81770

Reaktionsgleichung

2,4,6-triiodophenol

potassium carbonate

citronellol

triethylamine

methanesulfonyl chloride

→

desired product

Ausbeute 15.0%

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

Ausbeute 15.0%

Lösungsmittel

water

dimethylformamide

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   TrocknenThe dichloromethane layer was dried over magnesium sulfate
3. 3
   Waschenafter washing with saturated aqueous sodium chloride
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigeto give an oil
6. 6
   TemperaturThe mixture was heated to 100° C. for 30 minutes
7. 7
   Temperaturcooled to room temperature
8. 8
   SonstigeThe crude product was isolated
9. 9
   Sonstigeby partitioning the reaction mixture between water and dichloromethane
10. 10
    EinengenThe organic layer was concentrated under vacuum
11. 11
    Sonstigeto give an oil
12. 12
    SonstigeThe oil was purified

Vorschrift

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.

Quelle