Butyl bromide → 6-Butoxy-alpha-picoline

HRID 1587690Notes

Reaction equation

HRID 1587690 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[CH2:9](Br)[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:9]([O:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 178425782HCID 178425782, compound

Product 1

HCID 197561256-Butoxy-alpha-picolineYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 18.7 g (0.17 mol) of 6-hydroxy-2-methylpyridine (commercially available) and 24.0 g (0.17 mol) of n-butyl bromide dissolved in 100 ml of dimethylformamide was added 23.0 g (0.17 mol) of potassium carbonate, and the mixture was stirred at 90°-110° C. for 8 hours. To the mixture was added 300 ml of ice-water, and the mixture extracted with ethyl acetate, followed by a separation of the oily extract obtained by silica gel chromatography (ethyl acetate:hexane=7:97) to give 19.8 g of an oily substance (yield 69.9%).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. customfollowed by a separation of the
  3. extractionoily extract
  4. customobtained by silica gel chromatography (ethyl acetate:hexane=7:97)
  5. customto give 19.8 g of an oily substance (yield 69.9%)

Sources & evidence

ORD record
ord-8e23594586624b248469f1c6ac726d2b
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

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