HCID 86618198、化合物 → 7-(2-Hydroxy-3-phenylpropoxy)-3-(4-methoxyphenyl)chromen-4-one

HRID 1694662ノート

反応式

HRID 1694662 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]4[CH2:32][O:31]4)=[CH:23][CH:24]=3)[O:19][CH:18]=2)=[CH:13][CH:12]=1>O1CCCC1>[OH:31][CH:30]([CH2:32][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:29][O:28][C:22]1[CH:21]=[C:20]2[C:25]([C:26](=[O:27])[C:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=3)=[CH:18][O:19]2)=[CH:24][CH:23]=1

参加物

4

反応物 2

HCID 86618198HCID 86618198、化合物HCID 178418255HCID 178418255、化合物

生成物 1

HCID 672797737-(2-Hydroxy-3-phenylpropoxy)-3-(4-methoxyphenyl)chromen-4-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-40 °C

実験手順

To a solution of cuprous iodide (0.14 g, 0.74 mmol) in tetrahydrofuran (2 ml) was added phenylmagnesium bromide in tetrahydrofuran (1M, 2.22 ml, 2.22 mmol) dropwise at −40° C. After 5 minutes 3-(4-methoxyphenyl)-7-(oxiran-2-ylmethoxy)chromen-4-one (0.24 g, 0.74 mmol) in tetrahydrofuran (4 ml) was added slowly, and stirred at −40° C. for 1 hour. The mixture was quenched with saturated ammonium chloride and water, extracted with ethyl acetate, the organic layer washed with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The residue was purified by preparative thin layer chromatography, eluting with 10% methanol/methylene chloride, followed by ethyl acetate/hexane 2/3, to provide 7-(2-hydroxy-3-phenylpropoxy)-3-(4-methoxyphenyl)chromen-4-one.

後処理

  1. customThe mixture was quenched with saturated ammonium chloride and water
  2. extractionextracted with ethyl acetate
  3. washthe organic layer washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography
  7. washeluting with 10% methanol/methylene chloride

出典と根拠

ORDレコード
ord-2862fde44e37486ba03fe1aa1edac50a
出典データセット
uspto-grants-2012_04
特許番号
US08158810B2

反応ノート

読み込み中…