Benzene → 3-[2-Butyl-4-chloro-1-(4-nitrobenzyl)imidazol-5-yl]propenoic acid ethyl ester

HRID 466445

Reaktionsgleichung

Reaktionsgleichung von HRID 466445
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C:13]([CH:14]=O)=[C:12]([Cl:16])[N:11]=[C:10]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:25])=[O:24].[CH:46]1C=CC=C[CH:47]=1>>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C:13]([CH:14]=[CH:26][C:23]([O:25][CH2:46][CH3:47])=[O:24])=[C:12]([Cl:16])[N:11]=[C:10]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 3

HCID 241BenzeneHCID 10870911Carboxymethylene triphenylphosphoraneHCID 198153972-Butyl-5-chloro-3-(4-nitro-benzyl)-3h-imidazole-4-carbaldehyde

Produkt 1

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

Versuchsvorschrift

A mixture of 1.2 g of 1-(4-nitrobenzyl)-2-butyl-4-chloroimidazole-5-aldehyde and 1.5 g of (carboxymethylene)triphenylphosphorane in 50 mL of benzene was refluxed for 2 hours. The reaction mixture was concentrated and the residue was purified by flash column chromatography on silica gel (Hexane: EtOAc=3:1 elution). The major product, the E isomer, was eluted first and was obtained as a thick oil initially which solidified to give an amorphous solid, 1.2 g. The minor product, the Z isomer was eluted next and was isolated as a thick liquid, 85 mg. E isomer: NMR (200 MHz, CDCl3): 7.3 and 6.53 (d, 2H, 5=16 Hz); 5.3 (s, 2H); 2.62 (t, 2H, J=7.3 Hz); 1.69 (m, 2H); 1.28 (m, 5H); 0.89 (t, 3H, J=7.3 Hz). Z isomer: NMR (200 MHz, CDCl3): (key peaks only) δ 6.45 and 6.02 (d, 2H, J=11.8 Hz); 5.17 (s, 2H).

Aufarbeitung

  1. temperaturewas refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by flash column chromatography on silica gel (Hexane: EtOAc=3:1 elution)
  4. washThe major product, the E isomer, was eluted first
  5. customwas obtained as a thick oil initially which
  6. customto give an amorphous solid, 1.2 g
  7. washThe minor product, the Z isomer was eluted next
  8. customwas isolated as a thick liquid, 85 mg

Quellen und Nachweise

ORD-Eintrag
ord-5d810c67ce6f4ec7963267689a5925eb
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155118

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