반응 #84200

반응 방정식

ethyl 6-bromohexanoate

sodium hydride

3-(1-naphthoyl)-1H-indole

→

title compound 2

N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

용매

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGwith stirring over a period of 15 min
2. 2
   온도the mixture was then heated at 60° C. for 3 h
3. 3
   기타The solvent was removed under high vacuum
4. 4
   추출extracted by ethyl acetate (2×150 ml)
5. 5
   세척The combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml)
6. 6
   건조dried over sodium sulphate
7. 7
   여과filtered
8. 8
   농축concentrated to dryness
9. 9
   기타The crude product obtained
10. 10
    기타was purified by chromatography on silica gel

실험 절차

To a suspension of sodium hydride (1.1 g, 30 mmol, 60% in mineral oil) in DMF (100 ml) under nitrogen was added solid 3-(1-naphthoyl)-1H-indole 1 (5.43 g, 20 mmol). After stirring at room temperature for 1 h, a solution of ethyl 6-bromohexanoate (6.6 g, 30 mmol) in DMF (10 ml) was added slowly with stirring over a period of 15 min and the mixture was then heated at 60° C. for 3 h. The solvent was removed under high vacuum and the crude product was suspended in water (150 ml) and extracted by ethyl acetate (2×150 ml). The combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml), dried over sodium sulphate filtered and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane/ethyl acetate (8/2) to give the title compound 2 as an oil which became solid in the cold (7.1 g, 86%).

출처