反应详情

温度

25 °C

To a suspension of 301 mg lithium wire (1/4 inch portions) in 10 ml tetrahydrofuran under nitrogen was added 6.72 ml diisopropylamine and 3.44 ml styrene while maintaining the temperature at 25° C. The mixture was stirred until all the lithium had dissolved (about four hours) and then cooled to -55° C. 3,5-Dimethylisoxazole (4.3 g) in 10 ml tetrahydrofuran was then added dropwise and the mixture stirred for an hour at -55° C. 4-(6-Bromohexyloxy)benzonitrile (12 g) in 10 ml tetrahydrofuran was then added dropwise over a period of one hour, and the mixture was allowed to warm to room temperature and stirred for three days. The solvent was removed in vacuo, the residue treated with 5% ammonium chloride solution and extracted with ether. The ether extracts were dried and concentrated, and the residue subjected to high pressure liquid chromatography with ether-hexane (1:1) mixture to give 3.9 g 5-[7-(4-cyanophenoxy)-heptyl]-3-methylisoxazole, used directly in the next reaction.

1. dissolutionhad dissolved (about four hours)
2. temperaturecooled to -55° C
3. temperatureto warm to room temperature
4. stirringstirred for three days
5. customThe solvent was removed in vacuo
6. additionthe residue treated with 5% ammonium chloride solution
7. extractionextracted with ether
8. dry with materialThe ether extracts were dried
9. concentrationconcentrated