Ammonium Chloride → 2-[2-(3,4-Dimethoxyphenyl)-4,5-dimethoxyphenyl]-4,4-dimethyl-2-oxazoline

HRID 1586290

반응식

HRID 1586290 반응식
[Mg].Br[C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[CH:7][CH:8]=1.CO[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:16]=1[C:25]1[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:12][O:11][C:5]1[CH:4]=[C:3]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:16]=2[C:25]2[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=2)[CH:8]=[CH:7][C:6]=1[O:9][CH3:10]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 5462224MagnesiumHCID 110974552-(2,4,5-Trimethoxyphenyl)-4,4-dimethyl-2-oxazoline

생성물 1

HCID 212181682-[2-(3,4-Dimethoxyphenyl)-4,5-dimethoxyphenyl]-4,4-dimethyl-2-oxazoline수율 92.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In tetrahydrofuran (100 ml), magnesium (1.3 g) was reacted with 4-bromoveratrole (13 g) to prepare a Grignard reagent. While cooling in an ice-water bath, a solution of 2-(2,4,5-trimethoxyphenyl)-4,4-dimethyl-2-oxazoline (7.7 g) in tetrahydrofuran (100 ml) was added thereto. After stirring at room temperature for 48 hours, an aqueous saturated ammonium chloride solution (150 ml) was added and stirred for 15 minutes. Then, the mixed solution was separated to extract the aqueous layer with tetrahydrofuran (150 ml). The organic layers were combined each other and concentrated by an evaporator. The residue was dissolved in 10% hydrochloric acid (100 ml), which was washed with diethyl ether. The aqueous layer was cooled in an ice-water bath, then neutralized by adding a 20% aqueous sodium hydroxide solution. It was extracted with ethyl acetate, washed with a saturated saline solution and then dried over sodium sulfate. The solvent was distilled off to give 10 g of 2-[2-(3,4-dimethoxyphenyl)-4,5-dimethoxyphenyl]-4,4-dimethyl-2-oxazoline as a pale brown oil.

후처리

  1. temperatureWhile cooling in an ice-water bath
  2. stirringstirred for 15 minutes
  3. customThen, the mixed solution was separated
  4. extractionto extract the aqueous layer with tetrahydrofuran (150 ml)
  5. concentrationconcentrated by an evaporator
  6. dissolutionThe residue was dissolved in 10% hydrochloric acid (100 ml)
  7. washwhich was washed with diethyl ether
  8. temperatureThe aqueous layer was cooled in an ice-water bath
  9. additionby adding a 20% aqueous sodium hydroxide solution
  10. extractionIt was extracted with ethyl acetate
  11. washwashed with a saturated saline solution
  12. dry with materialdried over sodium sulfate
  13. distillationThe solvent was distilled off

출처 및 근거

ORD 기록
ord-e56a5f572a494381af91b09235b78a70
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05942641

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