反応 #2460288

反応方程式

1-ethynylnaphthalene

1,2,2,6,6-pentamethylpiperidine

ethyl chloroformate

→

ethyl 1-naphthylpropiolate

収率 36.0%

溶媒

acetonitrile

—

ligroin

反応条件

後処理

1. 1
   その他First, ethyl 1-naphthylpropiolate was prepared
2. 2
   その他was sparged with nitrogen for 10 min
3. 3
   その他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
   洗浄The solution was washed three times with water
9. 9
   乾燥with brine, dried (Na2SO4)
10. 10
    濃縮concentrated
11. 11
    その他The crude product was purified by column chromatography

実験手順

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).

出典