Sulfuric Acid → 2-(2,5-Dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone

HRID 1387332노트

반응식

HRID 1387332 반응식
BrCC.[Mg].Br[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[CH3:21].[C:22]([C:24]1[CH:28]=[CH:27][O:26][N:25]=1)#N.S(=O)(=O)(O)[OH:30]>C1COCC1>[O:26]1[CH:27]=[CH:28][C:24]([C:22]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[O:30])=[N:25]1

참가 물질

7

반응물 5

HCID 1118Sulfuric AcidHCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 109462162-Bromobenzyl-(2,5-dimethylphenyl)etherHCID 226246101,2-Oxazole-3-carbonitrile

생성물 1

HCID 109028752-(2,5-Dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone수율 6.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
50 °C

실험 절차

THF (2 ml) and bromoethane (0.1 ml) were added to magnesium (0.49 g, 0.02 mol) in a stream of nitrogen, and the mixture was stirred at 50° C. for 10 minutes. Then, a mixture of 1-bromo-2-(2,5-dimethylphenoxymethyl)benzene (2.91 g, 0.01 mol) and THF (8 ml) was added at 50 to 60° C. over 30 minutes, and the mixture was stirred at 50 to 60° C. for 1 hour. After completion of the reaction, the reaction mixture was added to a mixture of 3-cyanoisoxazole (1.45 g, 0.015 mol) and THF (15 ml) at 20° C. or lower over 15 minutes, and then the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 2N sulfuric acid (200 ml) was added, and the mixture was extracted with ether. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone (0.20 g, 6.3%) as colorless crystals. mp. 90.5-92° C.

후처리

  1. additionwas added at 50 to 60° C. over 30 minutes
  2. stirringthe mixture was stirred at 50 to 60° C. for 1 hour
  3. customAfter completion of the reaction
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. additionwas added
  6. extractionthe mixture was extracted with ether
  7. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  10. customrecrystallized from n-hexane

출처 및 근거

ORD 기록
ord-c40893368ca443f49b9961e0f43b81ef
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268312B1

반응 노트

불러오는 중…