Dimethyl Sulfoxide → 6-(Methylsulfonyl)pyridin-3-ol

HRID 13430

反応式

HRID 13430 の反応式
[C:1]([O-:4])(=O)[CH3:2].[K+].CS(C)=O.BrC1C=[N:13][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][CH:16]=1.C(OCC)(=O)C>C(OCC)C.O>[CH3:20][S:17]([C:14]1[N:13]=[CH:2][C:1]([OH:4])=[CH:16][CH:15]=1)(=[O:19])=[O:18]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 517044Potassium AcetateHCID 134334245-Bromo-2-methanesulfonylpyridine

生成物 1

HCID 231451966-(Methylsulfonyl)pyridin-3-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

6.6 g of bis(pinacolate)diboron, 5.9 g of potassium acetate and 980 mg of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane complex were added to a dimethylsulfoxide (80 ml) solution of 4.72 g of 3-bromo-6-methanesulfonyl-pyridine, and the reaction liquid was stirred at 80° C. for 2 hours. Ethyl acetate and water were added to the reaction liquid, the insoluble substance was removed through filtration through Celite, and the organic layer was separated. The organic layer was washed with water and saturated saline, and dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. 60 ml of aqueous 5 N sodium hydroxide solution and 30 ml of aqueous 30% hydrogen peroxide solution were added to a tetrahydrofuran (200 ml) solution of the resulting residue at 0° C., and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with diethyl ether, and washed with water. The aqueous layer was made acidic with 5 N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was washed with a mixed solvent of chloroform and hexane to obtain the entitled compound as a brown solid.

後処理

  1. customthe reaction liquid
  2. customthe insoluble substance was removed through filtration through Celite
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. addition60 ml of aqueous 5 N sodium hydroxide solution and 30 ml of aqueous 30% hydrogen peroxide solution were added to a tetrahydrofuran (200 ml) solution of the resulting residue at 0° C.
  8. customthe reaction liquid
  9. stirringwas stirred overnight at room temperature
  10. customThe reaction liquid
  11. washwashed with water
  12. extractionextracted with ethyl acetate
  13. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  14. customthe solvent was evaporated away under reduced pressure
  15. washThe resulting residue was washed with a mixed solvent of chloroform and hexane

出典と根拠

ORDレコード
ord-8cb018741c2b4d8d9221b51b787d6e50
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

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