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

Temperatur

0 °C

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.

1. additionwas added dropwise
2. dry with materialThe dichloromethane layer was dried over magnesium sulfate
3. washafter washing with saturated aqueous sodium chloride
4. concentrationconcentrated in vacuo
5. customto give an oil
6. temperatureThe mixture was heated to 100° C. for 30 minutes
7. temperaturecooled to room temperature
8. customThe crude product was isolated
9. customby partitioning the reaction mixture between water and dichloromethane
10. concentrationThe organic layer was concentrated under vacuum
11. customto give an oil
12. customThe oil was purified

ORD-Eintrag

ord-442ff5ad23f04eaebc3212d26f6af6ad

Quelldatensatz

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05620677