Potassium Carbonate → 1-(2-(Cyclopropylmethoxy)-6-(4-methoxybenzyloxy)phenyl)ethanone

HRID 412217노트

반응식

HRID 412217 반응식
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[C:7]=2[C:13](=[O:15])[CH3:14])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[C:7]=2[C:13](=[O:15])[CH3:14])[CH2:2][CH2:3]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 222587731-(2-(Cyclopropylmethoxy)-6-hydroxyphenyl)ethanone

생성물 1

HCID 99233791-(2-(Cyclopropylmethoxy)-6-(4-methoxybenzyloxy)phenyl)ethanone수율 89.2%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 180Acetone용매

실험 절차

To a stirred solution of 1-{2-[(cyclopropylmethyl)oxy]-6-hydroxyphenyl}ethanone (56.3 g, 272 mmol) in acetone (1000 mL) was added potassium carbonate (188 g, 1364 mmol), 4-methoxybenzyl chloride (40.9 mL, 300 mmol) and tetrabutyl-ammonium iodide (20.2 g, 54.6 mmol). The mixture was stirred at reflux overnight. The reaction mixture was allowed to cool to room temperature, filtered on Celite®, and then the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The separated organic phase was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Then the resulting white solid was recrystallized from ethanol, collected by filtration, washed with ethanol, and dried under reduced pressure to give 1-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}ethanone as a white solid (79.2 g, yield; 89%).

후처리

  1. temperatureat reflux overnight
  2. filtrationfiltered on Celite®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe separated organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThen the resulting white solid was recrystallized from ethanol
  11. filtrationcollected by filtration
  12. washwashed with ethanol
  13. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-c3baa0b1adc5480e98b1c7812a07c97d
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562811B1

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