Bis(2-bromoethyl) ether → 4-[[8-Acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:19](=[O:21])[CH3:20])[C:12]([OH:18])=[CH:13][CH:14]=2)[CH:9]=1.[H-].[Na+].[Br:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30]Br>CN(C)C=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:19](=[O:21])[CH3:20])[C:12]([O:18][CH2:30][CH2:29][O:28][CH2:27][CH2:26][Br:25])=[CH:13][CH:14]=2)[CH:9]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Under an argon atmosphere, 2 g (0.007 mol) of 4-[(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]-butanoic acid methyl ester in 5 ml of anhydrous dimethylformamide was added to a suspension of 0.29 g of sodium hydride in 25 ml of anhydrous dimethylformamide. The mixture was stirred at room temperature for 20 minutes and then 7.7 g of bis-(2-bromoethyl)ether was added and the mixture was stirred at room temperature for 20 hours. The solvent was removed and residual oil was purified by high pressure liquid chromatography using 25% ethyl acetate-hexane to yield 1.6 g (54%) of 4-[[8-acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester as an oil.
Aufarbeitung
- stirringthe mixture was stirred at room temperature for 20 hours
- customThe solvent was removed
- customresidual oil was purified by high pressure liquid chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-cf323b28734b449fbb11a68703031ea6
- Quelldatensatz
- uspto-grants-1986_06
- Patentnummer
- US04594442
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