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

HRID 466446

Reaktionsgleichung

Reaktionsgleichung von HRID 466446
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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): δ 6.5-6.15 (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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-7860bd17a38b43d0b621102c9405d0ba
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155118

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