Iodine → 2-(4'-Isopropyl-5-methoxy-biphenyl-2-yl)-4,4-dimethyl-4,5-dihydro-oxazole

HRID 1267107Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1267107
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][CH:6]=1.CO[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[C:24]1[O:25][CH2:26][C:27]([CH3:30])([CH3:29])[N:28]=1.[NH4+].[Cl-]>CCOCC.C1COCC1>[CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[C:24]2[O:25][CH2:26][C:27]([CH3:29])([CH3:30])[N:28]=2)=[CH:6][CH:7]=1)([CH3:13])[CH3:12]

Komponenten

8

Edukt 5

HCID 807IodineHCID 114621-Bromo-4-isopropylbenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 124213352-(2,4-Dimethoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole

Produkt 1

HCID 185454762-(4'-Isopropyl-5-methoxy-biphenyl-2-yl)-4,4-dimethyl-4,5-dihydro-oxazoleAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of magnesium (0.69 g) in Et2O (5 mL) containing a trace of iodine was added dropwise a solution of 1-bromo4-isopropyl-benzene (5.97 g) in Et2O (50 mL). Following the addition, the mixture was heated under reflux for 1 hour. The resulting grignard solution was then carrefully added to a solution of 2-(2,4-dimethoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole (3.52 g) in THF (60 mL) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was then poured into saturated aqueous solution of NH4Cl and the mixture was extracted with Et2O, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with CH2Cl2/AcOEt (85/15) to give the title compound (3.5 g) as a pale yellow oil.

Aufarbeitung

  1. additionthe addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. extractionthe mixture was extracted with Et2O
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography
  9. washeluting with CH2Cl2/AcOEt (85/15)

Quellen und Nachweise

ORD-Eintrag
ord-cd1a4dc3af6c4c2e9f35784dbf9eda73
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06552022B1

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