반응 #81778

반응 방정식

ethyl 10-bromoundecanoate

3-iodophenol

potassium carbonate

EtOAc

→

ethyl 10-(3-iodophenoxy)-undecanoate

수율 33.3%

용매

DMF

DMF

—

hexanes

반응 조건

후처리

1. 1
   기타The reaction was immersed in an oil bath
2. 2
   온도the oil bath temperature was increased to 85° C
3. 3
   workup.STIRRINGAfter stirring for an additional 4 hrs at 85° C.
4. 4
   온도to cool
5. 5
   여과filtered through a pad of celite
6. 6
   기타evaporated in vacuo
7. 7
   세척The organic phase was washed with water (100 ml), 1M aqueous sodium hydroxide (100 ml), water (2×100 ml) and brine (100 ml)
8. 8
   건조dried (Na2SO4)
9. 9
   여과filtered
10. 10
    기타evaporated in vacuo
11. 11
    기타to provide crude ethyl 10-(3-iodophenoxy)-undecanoate which

실험 절차

To a stirred solution of ethyl 10-bromoundecanoate (9.7 g, 33.0 mmol) in dry DMF (66 ml) was added 3-iodophenol (7.99 g, 36.3 mmol) and potassium carbonate (5.02 g, 37.6 mmol). The reaction was immersed in an oil bath which was warmed to 75° C. over 0.5 hr. After stirring for 14 hrs under an N2 atmosphere, the oil bath temperature was increased to 85° C. After stirring for an additional 4 hrs at 85° C., the reaction was allowed to cool, diluted with DMF (200 ml), filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up in ether (500 ml). The organic phase was washed with water (100 ml), 1M aqueous sodium hydroxide (100 ml), water (2×100 ml) and brine (100 ml), dried (Na2SO4), filtered and evaporated in vacuo to provide crude ethyl 10-(3-iodophenoxy)-undecanoate which was contaminated with olefinic esters. Flash column chromatography (silica, 1-2%; EtOAc in hexanes) provide ethyl 10-(3-iodophenoxy)-undecanoate as a clear oil (4.75 g, 33.3%).

출처