Ethyl Acetate → Ethyl 2-ethoxycarbonyl-3-(5-{2-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxyphenyl]ethyl}-2-phenyl-1,3-oxazol-4-yl)propionate

HRID 2221615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221615
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH2:34]O)=[CH:17][CH:16]=1.S(Cl)(Cl)=O.[C:40]([O:43][CH2:44][CH3:45])(=[O:42])[CH3:41]>>[CH2:44]([O:43][C:40]([CH:41]([CH2:34][C:24]1[N:25]=[C:26]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[O:27][C:23]=1[CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:6][C:2]=2[CH3:1])=[CH:20][CH:19]=1)[C:40]([O:43][CH2:44][CH3:45])=[O:42])=[O:42])[CH3:45]

Komponenten

4

Edukt 3

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 69217381[5-[2-[4-(5-Methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-2-phenyl-4-oxazolyl]methanol

Produkt 1

HCID 23076445Ethyl 2-ethoxycarbonyl-3-(5-{2-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxyphenyl]ethyl}-2-phenyl-1,3-oxazol-4-yl)propionateAusbeute 53 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (5-{2-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxyphenyl]ethyl}-2-phenyl-1,3-oxazol-4-yl)methanol (0.78 g) and thionyl chloride (2 mL) was stirred at 0° C. for 30 min. After concentration of the reaction mixture, ethyl acetate was poured into the residue. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. To a solution of the obtained residue in tetrahydrofuran (10 mL) was added a mixture of diethyl malonate (1.36 g), sodium hydride (60% in oil, 0.33 g) and tetrahydrofuran (30 mL) at 0° C. After stirring at room temperature for 15 hr, the mixture was refluxed for 1 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give ethyl 2-ethoxycarbonyl-3-(5-{2-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxyphenyl]ethyl}-2-phenyl-1,3-oxazol-4-yl)propionate (0.55 g, yield 53%) as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Aufarbeitung

  1. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. additionTo a solution of the obtained residue in tetrahydrofuran (10 mL) was added
  5. additiona mixture of diethyl malonate (1.36 g), sodium hydride (60% in oil, 0.33 g) and tetrahydrofuran (30 mL) at 0° C
  6. stirringAfter stirring at room temperature for 15 hr
  7. temperaturethe mixture was refluxed for 1 hr
  8. additionThe reaction mixture was poured into water
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed successively with dilute hydrochloric acid and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-76b539aab92b4380bf271fa51edad854
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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