Methanol → 2-(2,5-dimethylphenoxymethyl)phenyl oxazol-5-yl ketone O-methyloxime

HRID 1004369노트

반응식

HRID 1004369 반응식
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CO.[CH3:22][C:23]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:24]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[N:36][O:37][CH3:38])[CH:34]=[O:35]>CCOCC>[CH3:38][O:37][N:36]=[C:33]([C:34]1[O:35][CH:12]=[N:11][CH:10]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][O:25][C:24]1[CH:39]=[C:40]([CH3:43])[CH:41]=[CH:42][C:23]=1[CH3:22]

참가 물질

6

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 538610512-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetaldehyde

생성물 1

HCID 544754822-(2,5-dimethylphenoxymethyl)phenyl oxazol-5-yl ketone O-methyloxime수율 44.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

p-Toluenesulfonylmethylisocyanide (0.23 g, 1.2 mmol), potassium carbonate (0.18 g, 1.3 mmol) and methanol (2 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetaldehyde (0.30 g, 1 mmol), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with brine (80 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl oxazol-5-yl ketone O-methyloxime (0.15 g, 44.6%) as colorless crystals.

후처리

  1. temperatureunder reflux for 2 hours
  2. additionwas added
  3. washthe mixture was washed with brine (80 ml) twice
  4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  7. customrecrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-2fca4876e97c401387c2e9de040c7d48
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048885

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