1-Bromopropane → HCID 15027467, compound

HRID 1090803Notes

Reaction equation

HRID 1090803 reaction equation
[Mg].[CH3:2][CH2:3][CH2:4]Br.[OH:6][C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[C:9](=[O:16])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[Cl-].[NH4+]>O1CCCC1>[OH:16][C:9]([C:8]1[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=1[OH:6])([CH2:2][CH2:3][CH3:4])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 25517Ammonium ChlorideHCID 4122933Ethanone, 1-(2-hydroxyphenyl)-2-(1H-imidazol-1-yl)-HCID 5462224Magnesium

Product 1

HCID 15027467HCID 15027467, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution of Grignard reagent prepared from 73 mg of magnesium and 369 mg of n-propyl bromide, 202 mg of 1-(2-hydroxyphenacyl) imidazole (II) was added dropwise under ice-cooled conditions while stirring, and the mixture was refluxed for 2 hours. After icecooling, an aqueous solution of ammonium chloride was added to the mixture to decompose the surplus amount of the Grignard reagent and addition salts produced in the reaction. Extraction with chloroform was performed on this mixture and the chloroform layer was washed with water, followed by drying over anhydrous magnesium sulfate. The extract thus obtained was purified by means of silica gel column chromatography (eluent: chloroform) to produce 70 mg of the title compound at a yield of 29%.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooled conditions
  3. temperaturethe mixture was refluxed for 2 hours
  4. customproduced in the reaction
  5. extractionExtraction with chloroform
  6. washthe chloroform layer was washed with water
  7. dry with materialby drying over anhydrous magnesium sulfate
  8. extractionThe extract thus
  9. customobtained
  10. customwas purified by means of silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-41af7fa101a145f095cdd79f8f0b46ce
Source dataset
uspto-grants-1992_01
Patent number
US05082948

Reaction notes

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