Boron trifluoride etherate → 大豆甙元

HRID 418879

反应方程式

HRID 418879 反应方程式
[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

参与物

5

反应物 3

HCID 8000Boron trifluoride etherateHCID 31297甲基磺酰氯HCID 6400961-(2,4-二羟基苯基)-2-(4-羟基苯基)乙酮

产物 1

HCID 5281708大豆甙元

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂2 次

反应条件

温度
50 °C

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-3389877a413e4f5c9170966b8d4af98a
来源数据集
uspto-grants-2012_01
专利号
US08093273B2

关联笔记

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