Water → HCID 19916890, compound

HRID 1756131Notes

Reaction equation

HRID 1756131 reaction equation
[Mg].[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11]Br)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([N:20]1[C:24]([CH:25]=[O:26])=[CH:23][N:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1>[CH2:13]([N:20]1[C:24]([CH:25]([OH:26])[CH2:11][CH2:10][CH2:9][CH2:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:23][N:22]=[CH:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2596681-Bromo-4-phenylbutaneHCID 27732391-Benzyl-1H-imidazole-5-carboxaldehydeHCID 5462224Magnesium

Product 1

HCID 19916890HCID 19916890, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2,1 g of magnesium turnings are covered with 60 ml of dry tetrahydrofuran. A solution of 4-phenylbutylbromide (18,8 g) in 20 ml of dry tetrahydrofuran is then added dropwise to the mixture at such a rate that a smooth reaction is maintained. After the addition is complete, the reaction mixture is refluxed for one additional hour and cooled to room temperature. The reaction mixture is then added dropwise to a solution of 1-benzyl-5-imidazolecarbaldehyde (6,5 g) in 80 ml of tetrahydrofuran at 60° C. After the addition is complete, the reaction mixture is refluxed for 2 hours, cooled and poured into cold water. Tetrahydrofuran is evaporated and conc. hydrochloric acid is added to the solution. The product which is separated as an oil, is extracted with methylene chloride and evaporated to dryness.

Workup

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. additionAfter the addition
  4. temperaturethe reaction mixture is refluxed for one additional hour
  5. additionAfter the addition
  6. temperaturethe reaction mixture is refluxed for 2 hours
  7. temperaturecooled
  8. customTetrahydrofuran is evaporated
  9. additionconc. hydrochloric acid is added to the solution
  10. customThe product which is separated as an oil
  11. extractionis extracted with methylene chloride
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-d6df1ac3513c48b397ebeca8b9a48d68
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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