2-Methylbenzaldehyde → 2-{4-[1-(2-Methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline

HRID 1870432Notes

Reaction equation

HRID 1870432 reaction equation
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.[Mg].[C:16]1([CH3:24])[C:17]([CH:22]=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1>O1CCCC1>[CH3:24][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([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)[OH:23]

Participants

5

Reactant 3

HCID 107222-MethylbenzaldehydeHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole2×HCID 5462224Magnesium

Product 1

HCID 180010162-{4-[1-(2-Methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(4-bromophenyl)-4,4-dimethyl-2-oxazoline (1 g) in dry tetrahydrofuran (10 ml) are added dropwise magnesium (526 mg) and dry tetrahydrofuran (50 ml) under refluxing. The heating of the mixture is stopped, and thereto is added 2-(4-bromphenyl)-4,4-dimethyl-2-oxazoline (4 g) at a slowly refluxing rate, during which the mixture is stirred for 30 minutes, and then thereto is added o-tolualdehyde (2.16 ml) under ice-cooling. The mixture is stirred under ice-cooling for one hour, and stirred at room temperature for two hours, and the reaction is quenched with adding thereto a saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the organic layer is washed successively with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4~2:1) to give 2-{4-[1-(2-methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline (3.07 g) as white powder.

Workup

  1. temperatureunder refluxing
  2. temperatureThe heating of the mixture
  3. temperaturea slowly refluxing rate
  4. temperaturecooling
  5. stirringThe mixture is stirred under ice-
  6. temperaturecooling for one hour
  7. stirringstirred at room temperature for two hours
  8. customthe reaction is quenched
  9. additionwith adding
  10. extractionThe mixture is extracted with ethyl acetate
  11. washthe organic layer is washed successively with 1N hydrochloric acid
  12. dry with materiala saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate
  13. concentrationconcentrated
  14. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4~2:1)

Sources & evidence

ORD record
ord-b493c314a1cd46c7aeaa2dd962e9ef34
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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