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

HRID 279460노트

반응식

HRID 279460 반응식
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20][OH:21].[CH3:22][C:23]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:24]=1[O:25][CH2:26][C:27]([CH:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]1=[NH:38])(OC)C=O>CCOCC>[CH3:20][O:21][N:38]=[C:33]([C:14]1[O:17][CH:12]=[N:11][CH:10]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[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 867579072-(2,5-Dimethylphenoxymethyl)-alpha-methoxy-iminophenylacetaldehyde

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-methoxy-iminophenylacetaldehyde (0.30 g, 1 mmol), and the mixture 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-dimethylphenoxy-methyl)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-e9c62baa3625482da461529cac07e57b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362212B1

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