N-Formylmorpholine → HCID 59456278, compound

HRID 1873436Notes

Reaction equation

HRID 1873436 reaction equation
[Li]CCCC.[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[Se:21][CH:22]=[CH:23][CH:24]=3)=[C:16]([F:25])[C:15]=2[F:26])=[CH:10][CH:9]=1)[CH3:7].[CH:27](N1CCOCC1)=[O:28]>C1COCC1.ClCCl.Cl>[CH2:6]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[Se:21][C:22]([CH:27]=[O:28])=[CH:23][CH:24]=3)=[C:16]([F:25])[C:15]=2[F:26])=[CH:12][CH:13]=1)[CH3:7]

Participants

7

Reactant 3

HCID 20417N-FormylmorpholineHCID 594562952-(4'-Ethyl-2,3-difluorobiphenyl-4-yl)selenopheneHCID 178418339Butyllithium

Product 1

HCID 59456278HCID 59456278, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6.0 ml (35.3 mmol) of TMP are initially introduced at −20° C. in 30 ml of THF, and 21.5 ml (34.2 mmol, 15% soln. in hexane) of n-BuLi are metered in. After 30 min at this temperature, a solution of 11.8 g (34.0 mmol) of 2-(4′-ethyl-2,3-difluorobiphenyl-4-yl)selenophene in 70 ml of THF is added. When the addition is complete, the batch is warmed to RT and left at this temperature for 90 min. The solution is cooled to −60° C., and 3.6 ml (36.0 mmol) of N-formylmorpholine are added. The reaction mixture is warmed to RT and stirred for 2 h. The solution is diluted with a lot of dichloromethane, and 2 N hydrochloric acid is added. The mixture is washed with water, and the organic phase is separated off. The aqueous phase is extracted with dichloromethane, and the combined organic phases are washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is recrystallised from toluene. 5-(4′-Ethyl-2,3-difluorobiphenyl-4-yl)selenophene-2-carbaldehyde is obtained as a brown solid.

Workup

  1. additionWhen the addition
  2. waitleft at this temperature for 90 min
  3. temperatureThe solution is cooled to −60° C.
  4. temperatureThe reaction mixture is warmed to RT
  5. additionis added
  6. washThe mixture is washed with water
  7. customthe organic phase is separated off
  8. extractionThe aqueous phase is extracted with dichloromethane
  9. washthe combined organic phases are washed with sat. sodium chloride soln
  10. customThe solution is dried
  11. concentrationconcentrated to dryness
  12. customThe residue is recrystallised from toluene

Sources & evidence

ORD record
ord-11b2bc5ad16343a1ba94fccb9ecd9ab8
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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