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

HRID 1767306ノート

反応式

HRID 1767306 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 180Acetone溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b5476572a5fd4ed7abe652fd450e80c2
出典データセット
uspto-grants-2007_06
特許番号
US07232909B2

反応ノート

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