Toluene → HCID 68884464, Verbindung

HRID 1294332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294332
[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][CH2:14]C1C=CC(CO)=CC=1.[O:23]=[C:24]1[C:29]([CH2:30][C:31]([O:33]C)=[O:32])=[CH:28][CH:27]=[CH:26][NH:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O:63][CH2:64][CH3:65])=O)=NC(OCC)=O.[C:66]1([CH3:72])[CH:71]=CC=[CH:68][CH:67]=1>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:63][C:64]1[CH:65]=[CH:71][C:66]([CH2:72][O:23][C:24]2[C:29]([CH2:30][C:31]([OH:33])=[O:32])=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:67][CH:68]=1

Komponenten

7

Edukt 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 17861222HCID 17861222, VerbindungHCID 545680024-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethyl]benzyl alcohol

Produkt 1

HCID 68884464HCID 68884464, VerbindungAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]methanol (0.87 g), methyl 2-(2-oxo-1,2-dihydro-3-pyridyl)acetate (0.36 g), triphenylphosphine (0.87 g) and tetrahydrofuran (50 mL) was dropwise added a solution (40%, 1.47 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v). To a mixture of the obtained oil, tetrahydrofuran (3 mL) and methanol, (3 mL) was added an 1N aqueous sodium hydroxide solution (3 mL) and the mixture was stirred at room temperature for 2 hrs. 1N Hydrochloric acid (3 mL) and water were added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give crystals (0.14 g, 14%) of 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyloxy]-3-pyridyl]acetic acid from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 134-135° C.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customto give an oil from a fraction
  3. washeluted with ethyl acetate-hexane (1:3
  4. additionTo a mixture of the obtained oil, tetrahydrofuran (3 mL) and methanol, (3 mL)
  5. additionwas added an 1N aqueous sodium hydroxide solution (3 mL)
  6. stirringthe mixture was stirred at room temperature for 2 hrs
  7. addition1N Hydrochloric acid (3 mL) and water were added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aae04f1737cb4ecc803c8349e6cd9200
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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