Water → HCID 23333790, compound

HRID 904146Notes

Reaction equation

HRID 904146 reaction equation
[N:1]1([CH2:6][C:7]2[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[N:1]1([CH2:6][C:7]2[C:12]([O:13][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 20532704HCID 20532704, compound

Product 1

HCID 23333790HCID 23333790, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(imidazol-1-ylmethyl)-3-hydroxypyridine (3.0 g.) in dry N,N-dimethylformamide (40 ml.) was treated with sodium hydride (0.90 g., 50% suspension in mineral oil) at 0° C., while under a dry nitrogen atmosphere and the resulting suspension was stirred at 0° C. for a period of 30 minutes. Benzyl bromide (2.90 g.) was then added dropwise to the stirred solution and stirring of same was continued for a further hour at 0° C., followed by stirring at room temperature (~25° C.) for a period of two hours. At this point, water (10 ml.) was added to the mixture and the resulting aqueous solution was evaporated to dryness while under reduced pressure. The residue was taken up in chloroform and the inorganic material which remained was subsequently removed by means of filtration. The filtrate so obtained was then concentrated in vacuo and the residue subsequently chromatographed on silica gel. The resulting column was then eluted first with petroleum ether (b.p. 60°-80° C.) to remove the mineral oil and then with chloroform to remove the product. Evaporation of the chloroform solution then gave an oil, which subsequently crystallized on cooling. The latter material was then recrystallized from ethyl acetate/petroleum ether (b.p. 60°-80° C.) to afford pure 2-(imidazol-1-ylmethyl)-3-benzyloxypyridine (yield, 1.5 g.), m.p. 73°-74° C.

Workup

  1. stirringstirring
  2. waitof same was continued for a further hour at 0° C.
  3. stirringby stirring at room temperature (~25° C.) for a period of two hours
  4. customthe resulting aqueous solution was evaporated to dryness while under reduced pressure
  5. customthe inorganic material which remained was subsequently removed by means of filtration
  6. customThe filtrate so obtained
  7. concentrationwas then concentrated in vacuo
  8. customthe residue subsequently chromatographed on silica gel
  9. washThe resulting column was then eluted first with petroleum ether (b.p. 60°-80° C.)
  10. customto remove the mineral oil
  11. customwith chloroform to remove the product
  12. customEvaporation of the chloroform solution
  13. customthen gave an oil, which
  14. customsubsequently crystallized
  15. temperatureon cooling
  16. customThe latter material was then recrystallized from ethyl acetate/petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-60738ece10f346edae0fe157b87d8aa3
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

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