Boron trifluoride etherate → Daidzein

HRID 418879

反応式

HRID 418879 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 5281708Daidzein

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

In a solution of 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)-ethanone (2 mmol) in DMF (6 mL), freshly distilled 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.

後処理

  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

出典と根拠

ORDレコード
ord-3389877a413e4f5c9170966b8d4af98a
出典データセット
uspto-grants-2012_01
特許番号
US08093273B2

関連ノート

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