Tetrahydrofuran → 2-Nitro-4-(pentafluoroethyl)benzaldehyde

HRID 1873496ノート

反応式

HRID 1873496 の反応式
CN(C)/C=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].C1C[O:25]CC1>P([O-])([O-])([O-])=O>[N+:18]([C:6]1[CH:7]=[C:8]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:25])([O-:20])=[O:19]

参加物

4

反応物 2

HCID 8028TetrahydrofuranHCID 86623311HCID 86623311、化合物

生成物 1

HCID 573559322-Nitro-4-(pentafluoroethyl)benzaldehyde収率 52%

試薬・触媒・溶媒 1

HCID 1061Phosphate溶媒

実験手順

To a solution of crude (E)-N,N-dimethyl-2-(2-nitro-4-(perfluoroethyl)phenyl)ethenamine (12.2 g, 39.2 mmol) in THF (300 mL) and pH 7.2 phosphate buffer (300 mL) was added NaIO4 (29.3 g, 137.2 mmol). After 2.5 hours an aliquot (˜0.3 mL) was removed, filtered and dried. The proton NMR of this sample indicated that the reaction was complete. The solids were removed and the filter cake was washed with EtOAc. The filtrate was washed with brine (2×100 mL), dried and concentrated. The concentrate was purified via flash chromatography (100% hexane to 5% EtOAc) to provide 2-nitro-4-(perfluoroethyl)benzaldehyde (5.4 g, 52%).

後処理

  1. customAfter 2.5 hours an aliquot (˜0.3 mL) was removed
  2. filtrationfiltered
  3. customdried
  4. customThe solids were removed
  5. washthe filter cake was washed with EtOAc
  6. washThe filtrate was washed with brine (2×100 mL)
  7. customdried
  8. concentrationconcentrated
  9. customThe concentrate was purified via flash chromatography (100% hexane to 5% EtOAc)

出典と根拠

ORDレコード
ord-731b193bc88b4a35adf0a108b3fa9867
出典データセット
uspto-grants-2012_11
特許番号
US08304407B2

反応ノート

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