반응 #170764

반응 방정식

carbon monooxide

water

1-(1-trifluoromethanesulfonyloxyvinyl)cyclopropane carboxylic acid methyl ester

N,N-dimethylformamide methanol

triethylamine

carbon monooxide

→

titled compound

1-(1-Methoxycarbonylvinyl)cyclopropanecarboxylic acid methyl ester

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타at room temperature
2. 2
   기타the air in reaction vessel
3. 3
   온도cooled to room temperature
4. 4
   여과the mixture was filtered through Celite
5. 5
   세척subjected to elution with ethyl acetate
6. 6
   추출The filtrate was extracted with ethyl acetate
7. 7
   세척the separated organic layer was washed with a saturated aqueous solution of sodium chloride
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   농축concentrated under reduced pressure
10. 10
    기타The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/1)

실험 절차

To a solution of 1-(1-trifluoromethanesulfonyloxyvinyl)cyclopropane carboxylic acid methyl ester (4.36 g) prepared in the previous step in N,N-dimethylformamide/methanol (1/2, 66 ml) were sequentially added triethylamine (6.4 ml) and bis(triphenylphosphine)palladium (II) dichloride (1.07 g) at room temperature, and the air in reaction vessel was replaced with carbon monooxide at normal pressure. This reaction solution was stirred at 50° C. for 18 hours, and then cooled to room temperature, and carbon monooxide in the reaction vessel was replaced with nitrogen. To this reaction mixture were added water and ethyl acetate, the mixture was filtered through Celite, and subjected to elution with ethyl acetate. The filtrate was extracted with ethyl acetate, the separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/1) to give the titled compound (720 mg).

출처