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

HRID 926502Notes

Reaction equation

HRID 926502 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[CH:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[N:13][CH:12]=1>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[OH:17])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 178505773HCID 178505773, compound

Product 1

HCID 13285820(3-Fluorophenyl)(pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3-Fluorophenyl)magnesium bromide (1 M in THF, 9.3 mL, 9.3 mmol) was added dropwise by syringe to a solution of nicotinaldehyde (0.88 mL, 9.3 mmol) in dry THF (20 mL) at 0° C. The reaction mixture was stirred while warming to room temperature for 30 minutes, then quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate once and the organic layer was washed with water three times. The combined organic layers were dried (Na2SO4), filtered, and concentrated to dryness. The crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes) to provide the title compound.

Workup

  1. customquenched with saturated aqueous ammonium chloride solution
  2. customThe mixture was partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate once
  4. washthe organic layer was washed with water three times
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-68a9d39b29c5478fb441904648df473c
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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