N-Formylmorpholine → 5-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde

HRID 1873396

반응식

HRID 1873396 반응식
[Li]CCCC.[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[Se:16][CH:17]=[CH:18][CH:19]=2)=[C:11]([F:20])[C:10]=1[F:21])[CH3:7].[CH:22](N1CCOCC1)=[O:23]>C1COCC1.ClCCl.Cl>[CH2:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[Se:16][C:17]([CH:22]=[O:23])=[CH:18][CH:19]=2)=[C:11]([F:20])[C:10]=1[F:21])[CH3:7]

참가 물질

7

반응물 3

HCID 20417N-FormylmorpholineHCID 594563012-(4-Ethoxy-2,3-difluorophenyl)selenopheneHCID 178418339Butyllithium

생성물 1

HCID 594563155-(4-Ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

7.6 ml (44.4 mmol) of TMP are initially introduced at −20° C. in THF, and 26.7 ml (42.4 mmol, 15% soln. in hexane) of n-BuLi are metered in. After 25 min at this temperature, a solution of 11.7 g (38.6 mmol) of 2-(4-ethoxy-2,3-difluorophenyl)selenophene in 80 ml of THF is added. When the addition is complete, the batch is warmed to RT over the course of 45 min and left at this temperature for 20 min. The solution is cooled to −40° C., and N-formylmorpholine is added. The reaction mixture is warmed to RT and stirred for 4.5 h. The solution is diluted with a lot of dichloromethane, and 2 N hydrochloric acid is added. The mixture is briefly stirred vigorously, and the organic phase is separated off. The aqueous phase is extracted with dichloromethane, and the combined organic phases are washed with water. The solution is dried using sodium sulfate and concentrated to dryness. The residue is digested in cold ethanol, and the solid is filtered off with suction. Drying in vacuo gives 5-(4-ethoxy-2,3-difluorophenyl)selenophene-2-carbaldehyde as a violet solid.

후처리

  1. additionWhen the addition
  2. waitleft at this temperature for 20 min
  3. temperatureThe solution is cooled to −40° C.
  4. temperatureThe reaction mixture is warmed to RT
  5. additionis added
  6. stirringThe mixture is briefly stirred vigorously
  7. customthe organic phase is separated off
  8. extractionThe aqueous phase is extracted with dichloromethane
  9. washthe combined organic phases are washed with water
  10. customThe solution is dried
  11. concentrationconcentrated to dryness
  12. filtrationthe solid is filtered off with suction
  13. customDrying in vacuo

출처 및 근거

ORD 기록
ord-88a5c4f7866d4e3bb8f717dfa949ce84
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304036B2

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