3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[Hydroxy-(2,4,6-trimethyl-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

HRID 1712092Notes

Reaction equation

HRID 1712092 reaction equation
[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].[CH3:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[C:19]=1[Mg]Br>C1COCC1>[OH:2][CH:1]([C:19]1[C:20]([CH3:25])=[CH:21][C:22]([CH3:24])=[CH:23][C:18]=1[CH3:17])[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]

Participants

4

Reactant 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178425415HCID 178425415, compound

Product 1

HCID 592051913-{3-[Hydroxy-(2,4,6-trimethyl-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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 2,4,6-trimethylphenylmagnesium 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-(2,4,6-trimethyl-phenyl)-methyl]-pyridin-4-yl}-benzonitrile as white crystals.

Workup

  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

Sources & evidence

ORD record
ord-25bea7c1eeb54434a187d22aeeea023a
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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