反应 #2460288

反应方程式

1-ethynylnaphthalene

1,2,2,6,6-pentamethylpiperidine

ethyl chloroformate

→

ethyl 1-naphthylpropiolate

收率 36.0%

溶剂

acetonitrile

—

ligroin

反应条件

后处理

1. 1
   其他First, ethyl 1-naphthylpropiolate was prepared
2. 2
   其他was sparged with nitrogen for 10 min
3. 3
   其他The mixture was sparged with nitrogen for 10 min
4. 4
   温度heated
5. 5
   温度to reflux
6. 6
   温度at reflux for 2 h
7. 7
   温度The reaction mixture was cooled to ambient and
8. 8
   洗涤The solution was washed three times with water
9. 9
   干燥with brine, dried (Na2SO4)
10. 10
    浓缩concentrated
11. 11
    其他The crude product was purified by column chromatography

实验过程

First, ethyl 1-naphthylpropiolate was prepared. A mixture of 1-ethynylnaphthalene (7.7 g, 50.6 mmol), 4-(dimethylamino)pyridine (0.06 g, 0.5 mmol), 1,2,2,6,6-pentamethylpiperidine (8.8 g, 55.7 mmol), and acetonitrile (120 mL) was sparged with nitrogen for 10 min, and then tetrakis(triphenylphosphine)palladium(0) (1.3 g, 1.1 mmol) was added. The mixture was sparged with nitrogen for 10 min, heated to reflux, treated dropwise with ethyl chloroformate (12.1 g, 111.3 mmol), and held at reflux for 2 h. The reaction mixture was cooled to ambient and diluted with ligroin. The solution was washed three times with water and then with brine, dried (Na2SO4), and concentrated to deposit a brown oil. The crude product was purified by column chromatography to provide 4.0 g (36% of theory) of ethyl 1-naphthylpropiolate. 1H NMR (CDCl3): δ 1.40 (t, 3H), 4.33 (q, 2H), 7.50 (m, 3H), 7.90 (m, 3H), 8.30 (d, 1H).

来源