Diisopropylaluminium hydride → 3-[1-(4-Nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

HRID 465838

Reaction equation

HRID 465838 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][N:9]2[C:13]([CH:14]=[CH:15][C:16](OCC)=[O:17])=[C:12]([Cl:21])[N:11]=[C:10]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].C([Al+]C(C)C)(C)C>C1COCC1.CCOCC>[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][N:9]2[C:13]([CH2:14][CH:15]=[CH:16][OH:17])=[C:12]([Cl:21])[N:11]=[C:10]2[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 21896610Diisopropylaluminium hydrideHCID 536609323-[2-Butyl-4-chloro-1-(4-nitrobenzyl)imidazol-5-yl]propenoic acid ethyl ester

Product 1

HCID 665771703-[1-(4-Nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propen-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g of 3-[1-(4-nitrobenzyl)-2-butyl-4-chloroimidazol-5-yl]propenoic acid, ethyl ester, E isomer in 20 mL of THF was cooled with an ice bath, 1.7 mL of 1.5M diisopropylaluminum hydride (in toluene) was added slowly. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was then quenched with 3 mL of conc. NH4Cl solution and the mixture was stirred for an additional 30 minutes. During this period an extensive gel-like material formed. The reaction mixture was further diluted with ether and filtered through celite. The filtrate was concentrated and the crude product was purified by flash column chromatography on silica gel (Hexane:EtOAc=1:1 elution). The desired compound was obtained as a thick liquid; NMR (200 MHz, CDCl3): δ6.5-6.15 (m, 2H); 5.21 (s, 2H); 4.25 (d, 2H, J=4.5 Hz); 2.35 (t, 3H, J=7.4 Hz); 1.68 (m, 2H); 1.34 (m, 2H); 0.86 (t, 3H, J=7.4 Hz).

Workup

  1. customThe cooling bath was removed
  2. customThe reaction mixture was then quenched with 3 mL of conc. NH4Cl solution
  3. stirringthe mixture was stirred for an additional 30 minutes
  4. customDuring this period an extensive gel-like material formed
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by flash column chromatography on silica gel (Hexane:EtOAc=1:1 elution)

Sources & evidence

ORD record
ord-4fea9b9252ae4737a7fc33973d313d1b
Source dataset
uspto-grants-1992_10
Patent number
US05153197

Linked notes

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