Diisobutylaluminum hydride → HCID 22285566, Verbindung

HRID 1062441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062441
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:10]=[C:11]([C:13](OCC)=[O:14])[N:12]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH:10]=[C:11]([CH:13]=[O:14])[N:12]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 22285380HCID 22285380, Verbindung

Produkt 1

HCID 22285566HCID 22285566, VerbindungAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (200 mg, 0.51 mmol) in toluene (10 mL) at −78° C. was added DIBAH (2.0 mL) in toluene dropwise. The resulting solution was stirred at rt, quenched with 1N HCl (0.5 mL). The organic layer was washed with 1N HCl (5 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (50% EtOAc in hexane) to give the product (62 mg, 38% yield). LC-MS m/z 317.0 (MH+), retention time: 2.75 min (method 1).

Aufarbeitung

  1. customquenched with 1N HCl (0.5 mL)
  2. washThe organic layer was washed with 1N HCl (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (50% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-828f078a73d54489979c840ecee5e595
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960601B2

Notizen zur Reaktion

Wird geladen…