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Cesium carbonate → 2-(3-Formyl-2-methoxy-phenoxy)4-methoxy-benzonitrile

HRID 1178502
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HRID 1178502 반응식
F[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:12][C:13]1[C:14]([O:21][CH3:22])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C>[CH:16]([C:15]1[C:14]([O:21][CH3:22])=[C:13]([CH:20]=[CH:19][CH:18]=1)[O:12][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[O:17]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 6398782-Fluoro-4-methoxybenzonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

생성물 1

HCID 219303802-(3-Formyl-2-methoxy-phenoxy)4-methoxy-benzonitrile수율 74.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

2-Fluoro-4-methoxy-benzonitrile (0.28 g, 1.8 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.28 g, 1.8 mmol) and cesium carbonate (0.90 g, 2.4 mmol) were heated with stirring in dry DMF (4 mL) at 50° C. for 40 h. The reaction mixture was cooled, poured into 1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 1N sodium hydroxide solution (4×), water (4×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo to yield 2-(3-formyl-2-methoxy-phenoxy)-4-methoxy-benzonitrile (0.38 g, 73%) as a tan oil.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with 1N sodium hydroxide solution (4×), water (4×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-864cbf7fd3c849ada0c3462d9668c895
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07276528B2

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