3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[(4-Tert-butyl-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

HRID 2242124ノート

反応式

HRID 2242124 の反応式
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:2].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([Mg]Br)=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH:1]([OH:2])[C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]

参加物

4

反応物 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178440986HCID 178440986、化合物

生成物 1

HCID 592052063-{3-[(4-Tert-butyl-phenyl)-hydroxy-methyl]-pyridin-4-yl)-benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (30 mg, 0.15 mmol) in THF (1.5 mL) at −78° C. was added 2.0 M 4-tert-butylphenylmagnesium bromide in THF (0.15 mL). The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography eluted with 5% methanol in dichloromethane to yield 3-{3-[(4-tert-butyl-phenyl)-hydroxy-methyl]-pyridin-4-yl}-benzonitrile as a colorless oil.

後処理

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluted with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-3fd4fe8ca2e1482eb338fb97bce0115e
出典データセット
uspto-grants-2010_03
特許番号
US07671065B2

反応ノート

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