3-(3-Formyl-pyridin-4-yl)-benzonitrile → HCID 59205216, compound

HRID 2242114Notes

Reaction equation

HRID 2242114 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][Mg]Br>C1COCC1>[OH:2][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])[CH3:17]

Participants

4

Reactant 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 59205216HCID 59205216, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (30 mg) in THF (2 mL) at −78° C. was added 3.0 M methylmagnesium bromide in THF (0.144 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 to yield 3-[3-(1-hydroxy-ethyl)-pyridin-4-yl]-benzonitrile as a white foam.

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

Sources & evidence

ORD record
ord-728be98dfee14326b34152762129eed0
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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