Benzyl Bromide → (3-(Benzyloxy)-6-methylpyridin-2-yl)methanol

HRID 1359272

Reaction equation

HRID 1359272 reaction equation
[OH:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:17]([O:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1351283-Hydroxy-2-hydroxymethyl-6-methylpyridine

Product 1

HCID 22711808(3-(Benzyloxy)-6-methylpyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

100 g of 3-hydroxy-6-methyl-2-pyridine methanol and 150 g of potassium carbonate were suspended in 400 ml of N,N-dimethylformamide. Under heating under stirring 60° C. in an oil bath, 85 ml of benzyl bromide was added dropwise thereinto. Further, after heating under stirring for 30 minutes, insoluble matters were filtered off. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was recrystallized from ethanol/hexane, to give 145 g of the target compound.

Workup

  1. temperatureUnder heating
  2. temperatureFurther, after heating
  3. stirringunder stirring for 30 minutes
  4. filtrationinsoluble matters were filtered off
  5. additionWater was added to the filtrate
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. customThe residue was recrystallized from ethanol/hexane

Sources & evidence

ORD record
ord-9428576bcc0e46c2af241a37be4cb3bb
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Linked notes

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