Chloroform → 3-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazole-4-carbaldehyde

HRID 732103

Reaktionsgleichung

Reaktionsgleichung von HRID 732103
[CH:1]1([NH:4][C:5](=[NH:14])[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.Br[C:16](=[CH:19]OC(C)C)[CH:17]=[O:18].C([O-])([O-])=O.[K+].[K+].C(Cl)(Cl)Cl>O>[CH:1]1([N:4]2[C:16]([CH:17]=[O:18])=[CH:19][N:14]=[C:5]2[C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 534166342-Bromo-3-isopropoxy-propenalHCID 178491237HCID 178491237, Verbindung

Produkt 1

HCID 578380093-cyclopropyl-2-(4-methoxy-phenyl)-3H-imidazole-4-carbaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-cyclopropyl-4-methoxy-benzamidine (0.90 g, 4.75 mmol), 2-bromo-3-isopropoxy-propenal (1.37 g, 7.12 mmol) and K2CO3 (0.98 g, 7.12 mmol) were mixed with chloroform (10 ml) and water (1.2 ml), followed by stirring at r.t. for 24 h. After drying of the reaction mixture (Na2SO4), filtration and concentration of the filterate in-vacuo, the crude residue was purified via flash chromatography (40% EA in hex.) to isolate the title compound (973 mg, 85%). 1H-NMR: 9.83 (s, 1H), 7.82 (m, 3H), 7.02 (d, 2H), 3.89 (s, 3H), 3.58 (m, 1H), 1.13 (m, 2H), 0.64 (m, 2H).

Aufarbeitung

  1. dry with materialAfter drying of the reaction mixture (Na2SO4), filtration and concentration of the filterate in-vacuo
  2. customthe crude residue was purified via flash chromatography (40% EA in hex.)

Quellen und Nachweise

ORD-Eintrag
ord-59d3df64d5184e9fb6ce967002974f67
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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