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

HRID 1267107Notes

Reaction equation

HRID 1267107 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

HCID 185454762-(4'-Isopropyl-5-methoxy-biphenyl-2-yl)-4,4-dimethyl-4,5-dihydro-oxazoleYield 72.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-cd1a4dc3af6c4c2e9f35784dbf9eda73
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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