1-Bromopropane → HCID 15027467, compound

HRID 1650888Notes

Reaction equation

HRID 1650888 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 ice-cooling, 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. temperatureAfter ice-cooling
  5. customproduced in the reaction
  6. extractionExtraction with chloroform
  7. washthe chloroform layer was washed with water
  8. dry with materialby drying over anhydrous magnesium sulfate
  9. extractionThe extract thus
  10. customobtained
  11. customwas purified by means of silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-f4c849310bf747ff932bcabd58a2aff4
Source dataset
uspto-grants-1990_05
Patent number
US04925953

Reaction notes

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