HCID 17861257, Verbindung → HCID 68884209, Verbindung

HRID 1294207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294207
C([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:11][CH:10]=1)C1C=CC=CC=1>[C].[Pd].O1CCCC1>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:16][C:15]=1[CH2:14][O:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:28][CH:27]=1

Komponenten

4

Edukt 1

HCID 17861257HCID 17861257, Verbindung

Produkt 1

HCID 68884209HCID 68884209, VerbindungAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-chloromethyl-5-methyl-2-phenyloxazole (20.18 g), 4-benzyloxyphenol (17.70 g), anhydrous potassium carbonate (12.22 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 15 hrs. The reaction mixture was poured into water, and the precipitated solid was collected by filtration, and dried with air to give crystals (29.03 g, 88%) of 4-[(4-benzyloxyphenoxy)methyl]-5-methyl-2-phenyloxazole. Recrystallization from ethyl acetate-hexane gave colorless leaflet crystals. melting point: 126-127° C. A mixture of the obtained 4-[(4-benzyloxyphenoxy)methyl]-5-methyl-2-phenyloxazole (22.6 g), 5% palladium carbon (10.0 g) and tetrahydrofuran (300 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure to give crystals (16.3 g, 95%) of 4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenol. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 168-169° C.

Aufarbeitung

  1. customRecrystallization from ethyl acetate-hexane
  2. customgave colorless leaflet crystals
  3. customwas subjected to catalytic hydrogenation at room temperature
  4. filtrationAfter filtering off the catalyst
  5. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2e52a14c37b74449ab6096b1d69ffafc
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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