Imidazole → 5-(1H-Imidazol-1-yl)pentan-2-one

HRID 1439468Notes

Reaction equation

HRID 1439468 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5](=[O:7])[CH3:6].[NH:8]1[CH:12]=[CH:11][N:10]=[CH:9]1>C(#N)C>[CH2:2]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[CH2:3][CH2:4][C:5](=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 774932-Pentanone, 5-bromo-

Product 1

HCID 125919545-(1H-Imidazol-1-yl)pentan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-2-pentanone (1.65 g.) and imidazole (3.5 g.) in 15 ml. acetonitrile were stirred at 60° C. for 48 hours and the solvent removed. The residue was chromatographed on silica gel, eluting with 10% methanol in dichloromethane to give 1-(n-pentan-4-onyl)imidazole. This material in 40 ml. methanol was reduced with sodium borohydride in a similar manner to that described in Preparation 2A to give 1-(4-hydroxy-n-pentyl)imidazole.

Workup

  1. customthe solvent removed
  2. customThe residue was chromatographed on silica gel
  3. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-a5e17ed67ed742b68bb2e2232f3a8f97
Source dataset
uspto-grants-1977_11
Patent number
US04059705

Reaction notes

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