Ammonium Chloride → HCID 68709633, Verbindung

HRID 1441711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441711
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([C:27]2[S:28][CH:29]=[C:30]([CH2:32][CH2:33][CH:34]=[O:35])[N:31]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[CH3:16].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([C:27]2[S:28][CH:29]=[C:30]([CH2:32][CH2:33][CH:34]([C:2]3[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[OH:35])[N:31]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[CH3:16]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 903642-Bromo-3-methoxypyridineHCID 866183593-[2-(3,4-Diethoxyphenyl)thiazole-4-yl]propionaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 68709633HCID 68709633, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

A solution of 2-bromo-3-methoxypyridine (1.65 g, 8.78 mmol) in THF was cooled to −78° C., and 5.23 ml (8.16 mmol) of a 1.57 N solution of n-butyllithium in n-hexane was added dropwise. The resulting mixture was stirred at the same temperature for 45 minutes, and a solution (15 ml) of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]propionaldehyde (1.34 g, 4.39 mmol) in THF was added dropwise. After stirring at the same temperature for 30 minutes, the temperature of the mixture was raised to −30° C. over a period of 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated salt solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1). The solvent was distilled off under reduced pressure, and the residue was purified by preparative thin-layer silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2). The solvent was distilled off under reduced pressure, to thereby obtain 470 mg (yield: 26%) of 3-[2-(3,4-diethoxyphenyl)thiazole-4-yl]-1-(3-methoxypyridine-2-yl)-1-propanol as a yellow oil.

Aufarbeitung

  1. stirringAfter stirring at the same temperature for 30 minutes
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated salt solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/1)
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by preparative thin-layer silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)
  9. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f342b25cd8a94e9b87d5f646059df07a
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655680B2

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