1-Piperidinecarboxaldehyde → 4-Phenylpyridine-2-carboxaldehyde

HRID 594240

반응식

HRID 594240 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Li]CCCC.N1([CH:25]=[O:26])CCCCC1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[C:8]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH:25]=[O:26])[CH:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 1047002-Bromo-4-phenylpyridineHCID 178418339Butyllithium

생성물 1

HCID 122176544-Phenylpyridine-2-carboxaldehyde

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

A cooled (−78° C.) solution of commercially available 2-bromo-4-phenylpyridine (500 mg; 2.13 mmol) in anh. THF (9 ml) was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.33 ml; 2.13 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 1 h. Commercially available piperidine-1-carbaldehyde (483 mg; 4.27 mmol) was added dropwise to the cooled (−78° C.) reaction mixture, and stirring was continued at −78° C. for 15 min., and then at 0° C. for 1 h. Aq. sat. NH4Cl (25 ml) and AcOEt (50 ml) were added, and the separated organic layer was further washed with brine (20 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (toluene/AcOEt=7/3) afforded 4-phenylpicolinaldehyde as a yellow solid. LC-MS (conditions A): tR=0.43 min.; [M+H]+: 184.48 g/mol.

후처리

  1. temperaturecooled
  2. custom(−78° C.) reaction mixture
  3. stirringstirring
  4. waitwas continued at −78° C. for 15 min.
  5. waitat 0° C. for 1 h
  6. washthe separated organic layer was further washed with brine (20 ml)
  7. dry with materialdried over anh. MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure
  10. customPurification by FC (toluene/AcOEt=7/3)

출처 및 근거

ORD 기록
ord-91965e64d04c40d4b257646bbeddf5e0
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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