Toluene → N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenylacetamide
Reaktionsgleichung
[CH3:1][Mg]Br.[CH3:4][N:5]([CH3:21])[CH2:6][C:7]#[C:8][CH2:9][N:10](C(=O)C1C=CC=CC=1)[CH:11]=[O:12].[OH-:22].[Na+].[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)C.O1CCCC1>[CH3:21][N:5]([CH3:4])[CH2:6][C:7]#[C:8][CH2:9][NH:10][C:11](=[O:12])[C:30]([OH:22])([CH3:1])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
A solution of methylmagnesium bromide (10.23 m mol) in diethyl ether (3.5 ml) and tetrahydrofuran (5 ml) were added to a solution of N-(4-dimethylamino-2-butynyl)-benzoylformamide (0.50 g) in toluene (8 ml) at room temperature. After being heated at 70° C. for 1.5 hours, the mixture was treated with 1N aqueous solution of sodium hydroxide and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (15:1) as an eluent to give N-[4-dimethylamino-2-butynyl)-2-hydroxy-2-methyl-2-phenylacetamide (0.21 g).
Aufarbeitung
- extractionextracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol (15:1) as an eluent
Quellen und Nachweise
- ORD-Eintrag
- ord-3eda1f4f6210492fac622d0358177308
- Quelldatensatz
- uspto-grants-1993_03
- Patentnummer
- US05192779
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