4-Phenoxyphenol → 3-Cyclopropyl-5-[(4-phenoxyphenoxy)-methyl]-1,2,4-oxadiazole
Reaktionsgleichung
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[CH2:20][C:21]1[O:25][N:24]=[C:23]([CH:26]2[CH2:28][CH2:27]2)[N:22]=1>CN(C)C=O>[CH:26]1([C:23]2[N:22]=[C:21]([CH2:20][O:14][C:11]3[CH:10]=[CH:9][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:13][CH:12]=3)[O:25][N:24]=2)[CH2:28][CH2:27]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
While cooling, 5.58 g of 4-phenoxyphenol as a solution in 30 ml of absolute dimethylformamide is dripped into 1 g of 80% strength sodium hydride in 25 ml of absolute dimethylformamide. Upon completion of hydrogen evolution, 4.76 g of 5-chloromethyl-3-cyclopropyl-1,2,4-oxadiazole is dripped in and the mixture is stirred for 8 hours at 80° C. After the solvent has been removed, the residue is slurried in 250 ml of water, extracted three times, each time with 100 ml of ether, and the combined ethe phases are dried over sodium sulfate. After removal of the solvent under reduced pressure and recrystallization of the crude product from methanol/water (1:1) there is obtained 8.0 g of 3-cyclopropyl-5-[(4-phenoxyphenoxy)-methyl]-1,2,4-oxadiazole; m.p.: 99° C.
Aufarbeitung
- temperatureWhile cooling
- customAfter the solvent has been removed
- extractionextracted three times
- dry with materialeach time with 100 ml of ether, and the combined ethe phases are dried over sodium sulfate
- customAfter removal of the solvent
- customunder reduced pressure and recrystallization of the crude product from methanol/water (1:1) there
Quellen und Nachweise
- ORD-Eintrag
- ord-85d37d8ff6104c9d98cd71903fe9b389
- Quelldatensatz
- uspto-grants-1990_07
- Patentnummer
- US04943584
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