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Ammonium Chloride → 8-[4-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]-1,4-dioxaspiro[4,5]decan-8-ol

HRID 28386
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 28386
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[CH2:15]1[O:25][C:18]2([CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]2)[O:17][CH2:16]1.[NH4+].[Cl-]>C1COCC1>[CH3:13][C:11]1([CH3:14])[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:21]3([OH:24])[CH2:22][CH2:23][C:18]4([O:25][CH2:15][CH2:16][O:17]4)[CH2:19][CH2:20]3)=[CH:3][CH:4]=2)=[N:12]1
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Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Produkt 1

HCID 598367028-[4-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]-1,4-dioxaspiro[4,5]decan-8-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 8 g of 2-(4-bromophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole (31.5 mmol) in 15 ml of anhydrous THF is poured dropwise onto 956 mg of Mg (39.3 mmol) in such a way as to maintain the mixture at the reflux temperature and the mixture is refluxed for 2.5 hours. The mixture is cooled to room temperature and a solution of 5.41 g of 1,4-cyclohexandione monoethyleneacetal (34.65 mmol) in 20 ml of anhydrous THF is added to it dropwise. The mixture is stirred at room temperature for 1.5 hours and then at reflux temperature for 1 hour. The mixture is poured into 500 ml of a 10% NH4Cl solution and extracted with ethyl acetate. The organic phase is dried and, after filtration, the solvent is evaporated off under reduced pressure. The residue is crystallized in ethyl acetate. The product of the title is obtained in the form of a white solid.

Aufarbeitung

  1. temperatureto maintain the mixture at the reflux temperature
  2. temperaturethe mixture is refluxed for 2.5 hours
  3. temperatureat reflux temperature for 1 hour
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. filtrationafter filtration
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe residue is crystallized in ethyl acetate
  9. customThe product of the title is obtained in the form of a white solid

Quellen und Nachweise

ORD-Eintrag
ord-fbf95506f37f4ab1aab89c9847e6c956
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07419974B2

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