反应详情

A mixture of 1.99 g (10 mmol) of 2,6-dichloroquinoxaline, 2.13 g (11 mmol) of (E)-4-(4-hydroxyphenoxy)-2-penten-1-ol, 1.73 g (12.5 mmol) of powdered, anhydrous potassium carbonate and 50 ml of dry acetonitrile was warmed at reflux under nitrogen for a period of 3 hours. The mixture was cooled to room temperature, and the solid filtered off and washed well with ether. The filtrates were combined and evaporated to dryness, and the residue partitioned between ether and 2 percent aqueous sodium hydroxide. The aqueous layer was separated and extracted again with ether. The combined organic layers were washed with water, dried over MgSO4 and evaporated to dryness. The residual solid was purified by preparative scale HPLC, eluting with 7:3 hexane: ethyl acetate, to give a solid which was recrystallized from toluene. This gave 2.60 g (73%) of the desired pentenol as pale yellow crystals, having a melting point (m.p.) of 124°-126° C.

1. temperatureat reflux under nitrogen for a period of 3 hours
2. filtrationthe solid filtered off
3. washwashed well with ether
4. customevaporated to dryness
5. customthe residue partitioned between ether and 2 percent aqueous sodium hydroxide
6. customThe aqueous layer was separated
7. extractionextracted again with ether
8. washThe combined organic layers were washed with water
9. dry with materialdried over MgSO4
10. customevaporated to dryness
11. customThe residual solid was purified by preparative scale HPLC
12. washeluting with 7:3 hexane
13. customethyl acetate, to give a solid which
14. customwas recrystallized from toluene
15. customa melting point (m.p.) of 124°-126° C.