반응 #594881

반응 방정식

N-(2-(Thiophen-3-yl)ethyl)benzamide

phosphorous oxychloride

phosphorous pentoxide

→

oil

수율 92.6%

7-Phenyl-4,5-dihydrothieno[2,3-c]pyridine

수율 92.6%

용매

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 3 h
3. 3
   기타the volatiles were removed in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with cold water and ethyl acetate
5. 5
   workup.ADDITION5 N sodium hydroxide was added
6. 6
   기타the mixture and the layers were separated
7. 7
   추출The aqueous layer was extracted twice more with ethyl acetate
8. 8
   세척washed with aqueous solution of sodium bicarbonate, water
9. 9
   건조The organic layer was dried with sodium sulfate
10. 10
    기타purified by flash chromatography

실험 절차

N-(2-(Thiophen-3-yl)ethyl)benzamide (1.5 g, 6.48 mmol) suspended in xylenes (20 mL) was treated with phosphorous oxychloride (3.62 mL, 38 mmol) and phosphorous pentoxide (5.39 g, 19 mmol). The mixture was heated to reflux for 3 h and the volatiles were removed in vacuo. The residue was diluted with cold water and ethyl acetate. 5 N sodium hydroxide was added and the mixture and the layers were separated. The aqueous layer was extracted twice more with ethyl acetate. All the organic layers were combined and washed with aqueous solution of sodium bicarbonate, water, then brine. The organic layer was dried with sodium sulfate and purified by flash chromatography using a gradient of 20 to 60% of ethyl acetate in hexanes to afford a light yellow clear oil (1.28 g). MS (M+H)+ 214.

출처