반응 #2460288

반응 방정식

1-ethynylnaphthalene

1,2,2,6,6-pentamethylpiperidine

ethyl chloroformate

→

ethyl 1-naphthylpropiolate

수율 36.0%

용매

acetonitrile

—

ligroin

반응 조건

후처리

1. 1
   기타First, ethyl 1-naphthylpropiolate was prepared
2. 2
   기타was sparged with nitrogen for 10 min
3. 3
   기타The mixture was sparged with nitrogen for 10 min
4. 4
   온도heated
5. 5
   온도to reflux
6. 6
   온도at reflux for 2 h
7. 7
   온도The reaction mixture was cooled to ambient and
8. 8
   세척The solution was washed three times with water
9. 9
   건조with brine, dried (Na2SO4)
10. 10
    농축concentrated
11. 11
    기타The crude product was purified by column chromatography

실험 절차

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).

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