Reaktionsgleichung
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([O:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[N:29]>CN(C)C=O>[C:28]([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:3][C:4]1[CH:5]=[C:6]([O:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1)#[N:29]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Sodium hydride (24 mg, 1 mmol; 100%) was added to solution of 250 mg (0.855 mmol) of 2-chlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester, as prepared in step (c) of Example 1, in 2 mL of N,N-dimethylformamide. After 5 min, 130 μL (0.93 mmol) of 6-bromohexanenitrile was added to the reaction mixture. The reaction mixture was stirred for 2 h at ambient temperature, quenched with brine (50 mL), extracted into diethyl ether (50 mL), washed with water (3×10 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (methylene chloride/petroleum ether 4:1 to 100:0) to give 250 mg of the title compound as a colorless oil which solidified upon standing.
Aufarbeitung
- customquenched with brine (50 mL)
- extractionextracted into diethyl ether (50 mL)
- washwashed with water (3×10 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (methylene chloride/petroleum ether 4:1 to 100:0)
Quellen und Nachweise
- ORD-Eintrag
- ord-a32060e5af8244bdbee14082aca3e1e9
- Quelldatensatz
- uspto-grants-2001_08
- Patentnummer
- US06281206B1
Verknüpfte Notizen
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