Butyl bromide → HCID 13154052, compound

HRID 1587689Notes

Reaction equation

HRID 1587689 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[CH2:9](Br)[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:9]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 13154052HCID 13154052, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 11.0 g (0.10 mol) of 5-hydroxy-2-methylpyridine (commercially available), 13.8 g (0.10 mol) of n-butyl bromide and 6.00 g (0.04 mol) of anhydrous potassium carbonate with 100 ml of acetone was refluxed for 24 hours, the solvent was removed, 100 ml of water was added, and the mixture was extracted with chloroform. The chloroform layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under a reduced pressure. The residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:4) to give 8.00 g of an oily product (yield 47.9%).

Workup

  1. temperaturewas refluxed for 24 hours
  2. customthe solvent was removed
  3. addition100 ml of water was added
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-9fcea58064e948168763654c286ba2e2
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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