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

HRID 1712084노트

반응식

HRID 1712084 반응식
[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]

참가 물질

4

반응물 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178440986HCID 178440986, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ae69ec4fec6484797c25ed978457d99
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790895B2

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