2-Fluoropyridine → (4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

HRID 1930747Notes

Reaction equation

HRID 1930747 reaction equation
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[H-].[Na+]>CN(C)C=O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:9][OH:10])=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 97462-FluoropyridineHCID 115061,4-BenzenedimethanolHCID 24758Sodium hydride

Product 1

HCID 59255473(4-(Pyridin-2-yloxymethyl)-phenyl)-methanolYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 1,4-benzenedimethanol (5.5 g, 40 mmol), 2-fluoropyridine (1.3 g, 13 mmol) and N,N-dimethylformamide (15 mL) was added sodium hydride (1.4 g, 40 mmol, 66% in oil) at 0° C., which was stirred for 20 minutes at room temperature and for 1 hour at 70° C. To the reaction mixture was added water, and extraction was performed with ethyl acetate. The organic layer was washed with saturated saline, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the titled compound (1.9 g, 66%).

Workup

  1. additionTo the reaction mixture was added
  2. extractionwater, and extraction
  3. washThe organic layer was washed with saturated saline
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1)

Sources & evidence

ORD record
ord-00039949ee4840b1acc3d9ef4f9df8ad
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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