반응 #81770

반응 방정식

2,4,6-triiodophenol

potassium carbonate

citronellol

triethylamine

methanesulfonyl chloride

→

desired product

수율 15.0%

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

수율 15.0%

용매

water

dimethylformamide

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   건조The dichloromethane layer was dried over magnesium sulfate
3. 3
   세척after washing with saturated aqueous sodium chloride
4. 4
   농축concentrated in vacuo
5. 5
   기타to give an oil
6. 6
   온도The mixture was heated to 100° C. for 30 minutes
7. 7
   온도cooled to room temperature
8. 8
   기타The crude product was isolated
9. 9
   기타by partitioning the reaction mixture between water and dichloromethane
10. 10
    농축The organic layer was concentrated under vacuum
11. 11
    기타to give an oil
12. 12
    기타The oil was purified

실험 절차

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.

출처