반응 #159420

반응 방정식

1-formylpiperidine

n-BuLi

diisopropylamine

3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester

ammonium chloride

→

5-Formyl-3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester

용매

hexane

THF

THF

반응 조건

후처리

1. 1
   온도cooled to −78° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at −78° C. for 30 min
3. 3
   workup.STIRRINGthe mixture was again stirred at this temperature for 1.5 h
4. 4
   기타to reach room temperature
5. 5
   추출The aqueous phase was extracted several times with ethyl acetate
6. 6
   건조The combined organic phases were dried over sodium sulfate
7. 7
   기타the solvent was removed in vacuo
8. 8
   기타The product with the molecular weight of 281.0 (C9H6F3NO4S) was obtained in this way

실험 절차

A 1.6M n-BuLi solution in hexane (12 mL) was added dropwise to a solution of diisopropylamine (2.9 mL) in THF (30 mL) at −78° C. The reaction mixture was stirred at 0° C. for 10 min and then cooled to −78° C., and a solution of 3-(2,2,2-trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester (1.5 g) in THF (15 mL) was added. The reaction mixture was stirred at −78° C. for 30 min and then 1-formylpiperidine (4 g) was added, and the mixture was again stirred at this temperature for 1.5 h. Subsequently, saturated ammonium chloride solution was added and the reaction mixture was allowed to reach room temperature. The aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was removed in vacuo. The product with the molecular weight of 281.0 (C9H6F3NO4S) was obtained in this way; MS (ESI): 282 (M+H+).

출처