Dimethylformamide → 2-Methoxy-5-(trifluoromethoxy)benzaldehyde

HRID 1267881

반응식

HRID 1267881 반응식
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.C([Li])(C)(C)C.CN([CH:22]=[O:23])C>O1CCCC1>[CH3:11][O:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:9][C:8]=1[CH:22]=[O:23]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 27249731-Methoxy-4-(trifluoromethoxy)benzeneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehyde수율 72.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 4-(trifluoromethoxy)anisole (5.0 g, 26 mmol) in tetrahydrofuran (100 mL) cooled to −78° C. was slowly added a solution of tert-butyllithium in pentanes (23 mL, 1.7M, 39 mmol). The resulting solution was stirred at −78° C. for 30 minutes, before N,N′-dimethylformamide (8 mL, 104 mmol) was added. The solution was allowed to stir to ambient temperature and was then quenched with saturated aqueous ammonium chloride (100 mL). The suspension formed was extracted with ethyl acetate (2×100 mL) and the extracts dried (MgSO4). Concentration gave a yellow oil which was purified by silica chromatography to give the title compound as an oil (4.13 g, 18.8 mmol).

후처리

  1. additionwas added
  2. customwas then quenched with saturated aqueous ammonium chloride (100 mL)
  3. customThe suspension formed
  4. extractionwas extracted with ethyl acetate (2×100 mL)
  5. dry with materialthe extracts dried (MgSO4)
  6. concentrationConcentration
  7. customgave a yellow oil which
  8. customwas purified by silica chromatography

출처 및 근거

ORD 기록
ord-49f38f5c50f74b0ebbf7752bb7007ae5
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555552B2

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