Potassium Iodide → {4'-[2-(Ethylthio)ethoxy]-2',6'-dimethylbiphenyl-3-yl}methanol
Reaktionsgleichung
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]=2[CH3:17])[CH:6]=[CH:7][CH:8]=1.[CH2:18]([S:20][CH2:21][CH2:22]Cl)[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[CH2:18]([S:20][CH2:21][CH2:22][O:16][C:12]1[CH:11]=[C:10]([CH3:17])[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=2)=[C:14]([CH3:15])[CH:13]=1)[CH3:19]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 95 °C
Versuchsvorschrift
To a solution of 3′-(hydroxymethyl)-2,6-dimethylbiphenyl-4-ol (1.83 g, 8.00 mmol) and 2-chloroethyl ethyl sulfide (1.07 mL, 12.0 mmol) in N,N-dimethylformamide (15 mL) were added potassium carbonate (1.33 g, 9.60 mmol) and potassium iodide (0.132 g, 0.800 mmol), and the mixture was stirred at 95° C. for 24 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50) to give the title compound (1.19 g, yield 47%) as a colorless oil.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50)
Quellen und Nachweise
- ORD-Eintrag
- ord-32717a3ab3e14fdfa6034115093fb06f
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08492430B2
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