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

HRID 2266058

Reaktionsgleichung

Reaktionsgleichung von HRID 2266058
[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-a47d35d6715f44ddad022a47ffb151bf
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858632B2

Verknüpfte Notizen

Wird geladen…