Tetrahydrofuran → {6-[(5-Methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methanol
Reaktionsgleichung
[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:33]=[CH:32][C:18]2[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([C:22](OC)=[O:23])[O:21][C:17]=2[CH:16]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C>[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][O:14][C:15]1[CH:33]=[CH:32][C:18]2[C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:20]([CH2:22][OH:23])[O:21][C:17]=2[CH:16]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a mixture of methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate (32.70 g) and tetrahydrofuran (500 mL) was added dropwise diisobutylaluminum hydride (0.95M hexane solution, 235 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hrs, sodium sulfate decahydrate (71.85 g) was added, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate and the precipitate was filtered off. The filtrate was concentrated to give {6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methanol as colorless crystals (27.80 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 152-153° C.
Aufarbeitung
- stirringthe mixture was stirred at room temperature for 30 min
- filtrationthe precipitate was filtered off
- concentrationThe filtrate was concentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-48eacb6dc0624bcfb3d3467f721cbc3f
- Quelldatensatz
- uspto-grants-2008_05
- Patentnummer
- US07368578B2
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