3-Pyridinecarboxaldehyde → (3,4-Dimethoxyphenyl)(pyridin-3-yl)methanol

HRID 926570Notes

Reaction equation

HRID 926570 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[OH:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 103713-PyridinecarboxaldehydeHCID 178491916HCID 178491916, compound

Product 1

HCID 13475606(3,4-Dimethoxyphenyl)(pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(3,4-Dimethoxyphenyl)magnesium bromide (0.5 M in THF, 9.5 mL, 4.75 mmol) was added dropwise by syringe to a solution of nicotinaldehyde (0.88 mL, 9.37 mmol) in dry THF (20 mL) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C., then quenched with saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate. The separated aqueous phase was further extracted with ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes) to provide the title compound as a brown oil.

Workup

  1. customquenched with saturated aqueous ammonium chloride solution
  2. customThe mixture was partitioned between water and ethyl acetate
  3. extractionThe separated aqueous phase was further extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography (silica gel, 0-60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-363cc6f665cf43fe8d0a4447331502ff
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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