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

HRID 557259

Reaction equation

HRID 557259 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.CN(C)C=O.[H-].[Na+]>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

6

Reactant 4

HCID 6228DimethylformamideHCID 97462-FluoropyridineHCID 115061,4-BenzenedimethanolHCID 24758Sodium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-dimethyl formamide (15 mL) was added sodium hydride (1.4 g, 40 mmol, 66% in oil) at 0° C, which was stirred at room temperature for 20 minutes and at 70° C for one hour. To the reaction mixture was added water, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride water, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the title compound (1.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride water
  3. customthe solvent thereof was evaporated under a reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1)

Sources & evidence

ORD record
ord-e656e60029c0476ab312e1135b11d455
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Linked notes

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