Chlorosuccinimide → Ethyl 4-chloro-2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate

HRID 859244노트

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HRID 859244 반응식
[F:1][CH2:2][CH2:3][C:4]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15].[Cl:21]N1C(=O)CCC1=O>CN(C=O)C>[Cl:21][C:10]1[C:9]([O:13][CH3:14])=[CH:8][CH:7]=[C:6]2[C:11]=1[CH2:12][C:4]([CH2:3][CH2:2][F:1])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:5]2=[O:15]

참가 물질

4

반응물 2

HCID 31398Chlorosuccinimide3회HCID 16726730Ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate

생성물 1

HCID 16726731Ethyl 4-chloro-2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a solution of ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate (44.6 g, 159 mmol) in DMF (159 mL) was added N-chlorosuccinimide (23.4 g, 175 mmol) in portions. The solution was heated at 50° C. and the reaction was monitored periodically by NMR analysis of aliquots. After 6 hours, the reaction was approximately 80% complete by NMR analysis. The reaction mixture was allowed to cool to room temperature and stand overnight. After reheating to 50° C., additional N-chlorosuccinimide (2.12 g, 15.9 mmol) was added. Monitoring by NMR was continued, and after 4.5 hours another portion of N-chlorosuccinimide (2.12 g, 15.9 mmol) was added. After another 3 hours, the reaction was allowed to cool to room temperature and stand overnight. Most of the DMF was removed by evaporation at reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was washed with water (4 times) and brine and dried over Na2SO4. Filtration and removal of the solvent under reduced pressure gave crude ethyl 4-chloro-2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate. This material was used in the next step without purification.

후처리

  1. temperatureto cool to room temperature
  2. waitstand overnight
  3. customAfter reheating to 50° C.
  4. waitAfter another 3 hours
  5. temperatureto cool to room temperature
  6. waitstand overnight
  7. customMost of the DMF was removed by evaporation at reduced pressure
  8. customthe residue was partitioned between EtOAc and water
  9. washThe organic phase was washed with water (4 times) and brine
  10. dry with materialdried over Na2SO4
  11. filtrationFiltration and removal of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-eac1b06d88d245e396d9ff0bbec04f81
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07151196B2

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