N-Formylmorpholine → 5-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde

HRID 1873388노트

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HRID 1873388 반응식
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[Se:17][CH:18]=[CH:19][CH:20]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Li]CCCC.[CH:26](N1CCOCC1)=[O:27]>C(OCC)C.CC(OC)(C)C.Cl>[CH2:1]([CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[Se:17][C:18]([CH:26]=[O:27])=[CH:19][CH:20]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

참가 물질

7

반응물 3

HCID 20417N-FormylmorpholineHCID 594562962-[4-(4-Propylcyclohexyl)phenyl]selenopheneHCID 178418339Butyllithium

생성물 1

HCID 594562815-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 3283Diethyl Ether용매HCID 15413tert-Butyl methyl ether용매

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온도
-78 °C

실험 절차

1.48 g (4.47 mmol) of 2-[4-(4-propylcyclohexyl)phenyl]selenophene are initially introduced in 15 ml of diethyl ether, and 4.4 ml (7.0 mmol, 15% soln. in hexane) of n-BuLi are metered in rapidly. The mixture is heated under reflux for 15 min and subsequently cooled to −78° C. 1.4 ml (14.0 mmol) of N-formylmorpholine are added in one portion, and the mixture is warmed to RT and stirred for 24 h. The batch is diluted with MTBE, and 1 N hydrochloric acid is added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride solution and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is recrystallised from n-heptane. 5-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde is obtained as a red solid.

후처리

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 15 min
  3. temperaturethe mixture is warmed to RT
  4. additionis added
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is extracted with MTBE
  7. washThe combined organic phases are washed with sat. sodium chloride solution
  8. customdried
  9. concentrationThe solution is concentrated to dryness
  10. customthe residue is recrystallised from n-heptane

출처 및 근거

ORD 기록
ord-bc961fcae3eb4620bb82f7c616158a70
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304036B2

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