3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-[3-[Hydroxy-(2,5-dimethoxy-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

HRID 1712090ノート

反応式

HRID 1712090 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].[O:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[Mg]Br)[CH3:18]>C1COCC1>[OH:2][CH:1]([C:23]1[CH:24]=[C:19]([O:17][CH3:18])[CH:20]=[CH:21][C:22]=1[O:25][CH3:26])[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]

参加物

4

反応物 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178492591HCID 178492591、化合物

生成物 1

HCID 684988763-[3-[Hydroxy-(2,5-dimethoxy-phenyl)-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 (15 mg, 0.075 mmol) in THF (1 mL) at −78° C. was added 0.5 M 2,5-dimethoxylphenylmagnesium bromide in THF (0.3 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-[hydroxy-(2,5-dimethoxy-phenyl)-methyl]-pyridin-4-yl}-benzonitrile as white crystals.

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-96f9b496ff2143f1abdbf24d8a221b01
出典データセット
uspto-grants-2010_09
特許番号
US07790895B2

反応ノート

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