Water → 2-(Hydroxyphenyl-methyl)-6-methyl-pyridin-3-ol

HRID 228754

Reaction equation

HRID 228754 reaction equation
[OH:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>O1CCCC1>[OH:10][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[C:5]([CH3:8])[N:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 230783712-(Hydroxyphenyl-methyl)-6-methyl-pyridin-3-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-6-methyl-pyridine-2-carbaldehyde (350 mg) was dissolved in tetrahydrofuran (13 ml) to prepare a solution which was brought to −78° C. Phenylmagnesium bromide (7.4 ml) was slowly added dropwise thereto, and the mixture was stirred at room temperature for one hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give 2-(hydroxyphenyl-methyl)-6-methyl-pyridin-3-ol (553 mg, yield 100%).

Workup

  1. customto prepare a solution which
  2. customwas brought to −78° C
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was then washed with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-dbe8e2537f5a43f6abdac5e7d5c94209
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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