Water → 1-benzyl-5-(1-hydroxy-4,4-diphenylbutyl)-1H-imidazole

HRID 1756120Notes

Reaction equation

HRID 1756120 reaction equation
[Mg].Br[CH2:3][CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]([N:25]1[C:29]([CH:30]=[O:31])=[CH:28][N:27]=[CH:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1>[CH2:18]([N:25]1[C:29]([CH:30]([OH:31])[CH2:3][CH2:4][CH:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:28][N:27]=[CH:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 883331,1'-(3-Bromopropylidene)bisbenzeneHCID 27732391-Benzyl-1H-imidazole-5-carboxaldehydeHCID 5462224Magnesium

Product 1

HCID 148222901-benzyl-5-(1-hydroxy-4,4-diphenylbutyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2,0 g of magnesium turnings are covered with 60 ml of dry tetrahydrofuran. To the mixture is then added dropwise a solution of 1-bromo-3,3-diphenylpropane (22,9 g) in 20 ml of dry tetrahydrofuran 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 (7,35 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 to the solution is added conc. hydrochloric acid. The solution is cooled and the precipitate which contains the product as hydrochloride salt is removed by filtration, washed with water and dried. Yield 14,1 g. M.p. 160°-168° C.

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 and to the solution
  9. additionis added conc. hydrochloric acid
  10. temperatureThe solution is cooled
  11. customis removed by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-6d3ff6c475b2462dacf6425b90b7297c
Source dataset
uspto-grants-1995_08
Patent number
US05439928

Reaction notes

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