3-Pyridinecarboxaldehyde → Phenyl(pyridin-3-yl)methanol

HRID 509197

Reaction equation

HRID 509197 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1.C(OCC)(=O)C>[C:9]1([CH:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 234839Phenyl(pyridin-3-yl)methanolYield 98.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of nicotinaldehyde 75 (0.876 mL, 9.34 mmol) in THF (20 mL) at 0° C. was slowly added a 1M phenylmagnesium bromide solution (9.34 mL, 9.34 mmol) and the reaction mixture was allowed to warm to room temperature over 30 minutes. The crude solution was diluted with ethyl acetate and washed with water, dried over Na2SO4, filtered and concentrated to afford compound 76 (1.7 g, 98% yield) after purification by flash chromatography (50 to 100% EtOAc in hexanes).

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-465c2d8cab8547e098ef67278bd86b1c
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Linked notes

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