HCID 86618198, 화합물 → 7-(2-Hydroxy-3-phenylpropoxy)-3-(4-methoxyphenyl)chromen-4-one

HRID 1694662노트

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HRID 1694662 반응식
[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

참가 물질

4

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HCID 86618198HCID 86618198, 화합물HCID 178418255HCID 178418255, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
-40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2862fde44e37486ba03fe1aa1edac50a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158810B2

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