反应 #2314295

反应方程式

acetylene

4-Methyl-3-cyclohexenylacetylene

4-bromoanisole

triphenylphosphine

dipropylamine

→

4-(4-Methyl-3-cyclohexenylethynyl)anisole

溶剂

diisopropylamine

反应条件

后处理

1. 1
   其他To a round-bottom flask equipped with a stirbar
2. 2
   温度refluxing the slurry for 3 hours
3. 3
   其他to get a yellow slurry
4. 4
   温度refluxing 1 hour
5. 5
   温度cooling
6. 6
   其他A stream of dry nitrogen is bubbled through this solution for 15 minutes
7. 7
   其他to degas it
8. 8
   温度the solution is then refluxed under a nitrogen atmosphere for 5 hours
9. 9
   workup.ADDITIONThe cooled solution is poured onto silica gel
10. 10
    洗涤eluted with 1:1 hexanes
11. 11
    其他ethyl acetate to give the product
12. 12
    其他The methyl group may be removed

实验过程

To a round-bottom flask equipped with a stirbar is added acetylene 4F (R=methyl) (2 g), 4-bromoanisole (3.40 g), palladium catalyst (made by mixing together 29.11 g triphenylphosphine, 3.28 g PdCl2, and 200 mL dipropylamine; refluxing the slurry for 3 hours to get a yellow slurry; cooling to room temperature; adding 3.69 g copper (II) acetate monohydrate; refluxing 1 hour; cooling and storing in the freezer) (330 mg), and diisopropylamine (80 mL). A stream of dry nitrogen is bubbled through this solution for 15 minutes to degas it, and the solution is then refluxed under a nitrogen atmosphere for 5 hours. The cooled solution is poured onto silica gel and eluted with 1:1 hexanes:ethyl acetate to give the product. The methyl group may be removed using the conditions used for deprotection of methyl ether 2F.

来源