1-Bromohexane → HCID 19756143, compound

HRID 1587694Notes

Reaction equation

HRID 1587694 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][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(N(CC)C=O)C>[CH2:9]([O:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 178425782HCID 178425782, compound

Product 1

HCID 19756143HCID 19756143, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 12051DiethylformamideSolvent

Procedure

To a solution of 12.0 g (0.11 mol) of 6-hydroxy-2-methylpyridine (commercially available) and 18.2 g (0.11 mol) of n-hexyl bromide dissolved in 100 ml of N,N-diethylformamide was added 15.2 g (0.11 mol) of potassium carbonate, and the mixture was stirred at 80° to 90° C. for 8 hours. Into the resultant mixture was poured 300 ml of ice-water, the mixture was extracted with ethyl acetate, and the oily extract obtained was separated by silica gel column chromatography (ethyl acetate:hexane=1:9) to give 12.1 g of an oily substance (yield 57.0%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. extractionthe oily extract
  3. customobtained
  4. customwas separated by silica gel column chromatography (ethyl acetate:hexane=1:9)
  5. customto give 12.1 g of an oily substance (yield 57.0%)

Sources & evidence

ORD record
ord-c1b4cf7b550846a1a4f63b9a6997c351
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

Loading…