반응 #465565

반응 방정식

1-[1-(1-methylethyl)-1,2,3,4-tetrahydro-quinolin-6-yl)ethanone

sodium hydride

ethyl 2-fluoro-diethylphosphonoacetate

ammonium chloride

→

title compound

ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoate

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도under cooling with ice
2. 2
   온도under cooling with ice for 30 minutes
3. 3
   workup.STIRRINGThe obtained mixture was stirred
4. 4
   온도under cooling with ice for one hour
5. 5
   추출The obtained mixture was extracted with ethyl acetate
6. 6
   세척the organic phase was washed with a saturated aqueous solution of common salt
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   농축concentrated in a vacuum
9. 9
   기타The residue was purified by silica gel column chromatography

실험 절차

450 mg (60%, 12 mmol) of sodium hydride was suspended in 10 ml of N,N-dimethylformamide. 3.3.g (14 mmol) of ethyl 2-fluoro-diethylphosphonoacetate was dropped into the suspension under cooling with ice. The obtained mixture was stirred under cooling with ice for 30 minutes, followed by the addition of 2.0 g (9.2 mmol) of 1-[1-(1-methylethyl)-1,2,3,4-tetrahydro-quinolin-6-yl)ethanone. The obtained mixture was stirred under cooling with ice for one hour, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate, and the organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography to give 2.3 g of the title compound as a colorless oil.

출처