Reaktionsgleichung
[CH3:1][Mg]I.[C:4]([C:7]1[N:8]=[C:9]([CH2:33][CH2:34][CH2:35][CH3:36])[N:10]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[C:12]#[N:13])(=[O:6])[CH3:5].[Cl-].[NH4+]>O1CCCC1>[CH2:33]([C:9]1[N:10]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:11]([C:12]#[N:13])=[C:7]([C:4]([OH:6])([CH3:1])[CH3:5])[N:8]=1)[CH2:34][CH2:35][CH3:36]Komponenten
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
1 ml of a 2M solution of methylmagnesium iodide in tetrahydrofuran was added dropwise at room temperature, whilst stirring, to a solution of 840 mg of 4-acetyl-2-butyl-5-cyano-1-tritylimidazole [prepared as described in Preparation 5(ii)] in 15 ml of tetrahydrofuran, and the resulting mixture was stirred at 40° C. for 1 hour. The mixture was cooled, and then a saturated aqueous solution of ammonium chloride was added to it dropwise. The tetrahydrofuran layer was separated and concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 539 mg of the title compound as a colorless solid, melting at 151°-152° C.
Aufarbeitung
- temperatureThe mixture was cooled
- customThe tetrahydrofuran layer was separated
- concentrationconcentrated by evaporation under reduced pressure
- customThe concentrate was purified by column chromatography through silica gel
- additionby volume mixture of hexane and ethyl acetate as the eluent
Quellen und Nachweise
- ORD-Eintrag
- ord-56c2775e83704fca903ab9751772b843
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05616599
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