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

HRID 478340

反応式

HRID 478340 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-95e7f7bf20354914a3de5c0ed035316e
出典データセット
uspto-grants-2003_11
特許番号
US06642223B2

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