Benzyl Bromide → HCID 86747873, compound

HRID 1033891Notes

Reaction equation

HRID 1033891 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:7](/[CH:10]=[CH:11]/[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[CH:26]([N-]C(C)C)([CH3:28])[CH3:27].[Li+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O1[CH2:46][CH2:45][CH2:44][CH2:43]1>[Cl-].[NH4+]>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:7](/[CH:10]=[CH:11]/[C:12]([CH2:43][C:44]2[CH:28]=[CH:26][CH:27]=[CH:46][CH:45]=2)([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 86747871HCID 86747871, compound

Product 1

HCID 86747873HCID 86747873, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

A solution of ethyl (E)-4-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-3-butenoate (256 mg, 0.709 mmol) in tetrahydrofuran (5 mL) was cooled to -78° C. under argon, and lithium diisopropylamide (0.85 mmol, 1 M in tetrahydrofuran) was added. After 10 minutes benzyl bromide (243 mg, 1.42 mmol) was added. The mixture was then stirred at room temperature overnight, diluted with 10% ammonium chloride and extracted with ethyl acetate. The dried, concentrated product was chromatographed over silica gel with 6:4 hexane/ethyl acetate to give 128 mg (33%) of the title compound as an oil. NMR indicated the bis(benzyl) substitution.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe dried, concentrated product was chromatographed over silica gel with 6:4 hexane/ethyl acetate

Sources & evidence

ORD record
ord-5fc87e96813443c297910ffdd6f210c1
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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