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

HRID 1267881ノート

反応式

HRID 1267881 の反応式
[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]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 27249731-Methoxy-4-(trifluoromethoxy)benzeneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehyde収率 72.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-49f38f5c50f74b0ebbf7752bb7007ae5
出典データセット
uspto-grants-2003_04
特許番号
US06555552B2

反応ノート

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