Boron trifluoride etherate → Daidzein

HRID 884733

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HRID 884733 반응식
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.B(F)(F)F.[CH3:23]COCC.CS(Cl)(=O)=O>CN(C=O)C>[OH:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9](=[O:18])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:23][O:1]2)=[CH:4][CH:5]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 31297Methanesulfonyl chlorideHCID 6400962,4,4'-Trihydroxydeoxybenzoin

생성물 1

HCID 5281708Daidzein

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
50 °C

실험 절차

In a solution of 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)-ethanone (2 mmol) in DMF (6 mL), freshly destilled BF3.OEt2 (6.3 mL) was added under argon. The mixture was heated at 50° C., and a solution of methanesulphonyl chloride (1 mL) in dry DMF (1.5 mL) was added slowly. After reaction at 80° C. for 1 h, the mixture was cooled to rt and poured into a large volume of ice cold aq. sodium acetate (12 g/100 mL), then extracted with EtOAc, and the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel using a mixture of DCM and MeOH to give 7-hydroxy-3-(4-hydroxyphenyl)-chromen-4-one.

후처리

  1. customAfter reaction at 80° C. for 1 h
  2. temperaturethe mixture was cooled to rt
  3. extractionextracted with EtOAc
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of DCM and MeOH

출처 및 근거

ORD 기록
ord-a49de2df1a8541368fd5a62faf6e5b39
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242130B2

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