Water → HCID 178487492, Verbindung

HRID 1368510

Reaktionsgleichung

[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=2)=[O:7])[N:3]=[CH:2]1.[CH:20]([Mg]Cl)([CH3:22])[CH3:21].[Cl-].[NH4+].O>C1COCC1>[NH:1]1[CH:5]=[C:4]([C:6]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=3)[CH:9]=2)([OH:7])[CH:20]([CH3:22])[CH3:21])[N:3]=[CH:2]1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

(1H-Imidazol-4-yl)-(6-methoxynaphthalen-2-yl)ketone (6.50 g) was dissolved in THF (120 ml), and the solution was cooled to −10° C. To the solution was slowly added dropwise a solution of isopropyl magnesium chloride in THF (2.0 M; 38.7 ml), and the mixture was stirred at −10° C. for 30 min. To the reaction mixture was added saturated aqueous solution of ammonium chloride and water. The mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium chloride, dried and concentrated. The residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1→10:1). Recrystallization from ethyl acetate gave the titled compound (5.04 g) as a colorless crystalline powder.

Aufarbeitung

extractionThe mixture was extracted with ethyl acetate
washThe extract was washed with saturated aqueous solution of sodium chloride
customdried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent, chloroform:methanol=20:1→10:1)
customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-e95ae7f9ea34473b9c5e4a42c73f0396
Quelldatensatz: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06573289B1

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