Dimethylformamide → 4-(Pyridin-3-yloxy)benzaldehyde

HRID 640295노트

반응식

HRID 640295 반응식
CN(C)C=O.[OH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:8]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

생성물 1

HCID 46774194-(Pyridin-3-yloxy)benzaldehyde수율 27.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

To an N,N-dimethylformamide (30.0 mL) solution of 3-hydroxypyridine (3.00 g, 31.5 mmol) and 4-fluorobenzaldehyde (5.08 g, 41.0 mmol) was added potassium carbonate (8.71 g, 63.0 mmol) under nitrogen atmosphere, which was stirred for 17 hours at 70° C. The reaction mixture was then cooled to room temperature and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1→3:1) to obtain the title compound (1.70 g, 27.1%).

후처리

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1→3:1)

출처 및 근거

ORD 기록
ord-93934173cb974a0992ef8ec96cff018f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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