1,2-Dibromoethane → 2-[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole

HRID 81732

Reaktionsgleichung

Reaktionsgleichung von HRID 81732
[Mg].BrCCBr.Br[CH:7]([CH3:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O1CCN=C1.[CH3:21][C:22]1([CH3:39])[CH2:26][O:25][C:24]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[CH:29][C:28]=2OC)=[N:23]1>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:36][O:35][C:30]1[C:31]([O:33][CH3:34])=[CH:32][C:27]([C:24]2[O:25][CH2:26][C:22]([CH3:21])([CH3:39])[N:23]=2)=[C:28]([CH:7]([CH3:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:29]=1

Komponenten

7

Edukt 4

HCID 78391,2-DibromoethaneHCID 102754(2-Bromopropyl)benzeneHCID 5462224MagnesiumHCID 670534204,4-Dimethyl-2-(2,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazole oxazoline

Produkt 1

HCID 595987102-[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-4,4-dimethyl-4,5-dihydro-oxazoleAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a rapidly stirring suspension of magnesium turnings (1.32 g, 54.5 mol) and in 35 mL tetrahydrofuran (THF) was added 1,2-dibromoethane (0.10 mL) in one portion. 2-bromo-1-phenylpropane (10.86 g, 54.5 mmol) was added at a rate that maintained the internal temperature at 40° C. After 2.5 hours the cloudy suspension was transferred via canula to a solution of 4,4-dimethyl-2-(2,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazole oxazoline (10.013 g, 36.4 mmol) in 50 mL THF. After 18 hours the solution cooled to 0° C. and quenched by the slow addition of 10% NH4Cl. 500 mL H2O was added and the mixture was extracted with ethyl acetate, washed with H2O, and washed with brine. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purifications via flash chromatography (4:1 hexane/ethyl acetate) afforded 2-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole as a clear viscous oil (7.833 g, 41%).

Aufarbeitung

  1. temperatureAfter 18 hours the solution cooled to 0° C.
  2. customquenched by the slow addition of 10% NH4Cl
  3. addition500 mL H2O was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with H2O
  6. washwashed with brine
  7. dry with materialThe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a crude solid

Quellen und Nachweise

ORD-Eintrag
ord-49b53bc6a1ed452f8ff89099cdf5a23e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846705B2

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