Hydrogen Peroxide → 3-(2-Hydroxyethyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 452218노트

반응식

HRID 452218 반응식
C12BC(CCC1)CCC2.[CH3:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]=[CH2:27])[C:21]1=[O:28].[OH-].[Na+].OO.S(OS([O-])=O)([O-])=[O:34].[Na+].[Na+]>O1CCCC1.O>[OH:34][CH2:27][CH2:26][C:22]1[C:21](=[O:28])[N:20]([C:12]2[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:11]=2[CH3:10])[CH:25]=[CH:24][CH:23]=1

참가 물질

8

반응물 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24346Disodium disulfiteHCID 789669-Borabicyclo(3.3.1)nonaneHCID 594101981-(2-Methyl-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

생성물 1

HCID 569267333-(2-Hydroxyethyl)-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

With ice-cooling, a solution of 40 g (326 mmol) of 9-borabicyclo[3.3.1]nonane in 650 ml of tetrahydrofuran is added over a period of 45 min to 38 g (148 mmol) of the compound from Example 23A. The mixture is stirred at this temperature for another hour, and a solution of 30 g (747 mmol) of sodium hydroxide in 740 ml of water is then added over a period of 15 min. 151 ml of a 30% strength hydrogen peroxide solution are added such that the temperature does not exceed 30° C. After the addition has ended, the cooling is removed and stirring is continued for a further 30 min. The mixture is repeatedly extracted with ethyl acetate, the combined organic phases are washed with a solution of 780 g (1.63 mol) of sodium disulphite, the organic phase is separated off and the aqueous phase is again extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is applied to silica gel and chromatographed using a gradient of cyclohexane and ethyl acetate. The product-containing fractions are combined and concentrated to dryness under reduced pressure. This gives 38 g (93% of theory) of the desired product.

후처리

  1. temperatureWith ice-cooling
  2. customdoes not exceed 30° C
  3. additionAfter the addition
  4. customthe cooling is removed
  5. stirringstirring
  6. extractionThe mixture is repeatedly extracted with ethyl acetate
  7. customthe organic phase is separated off
  8. extractionthe aqueous phase is again extracted with ethyl acetate
  9. washThe combined organic phases are washed with saturated sodium chloride solution
  10. dry with materialdried over magnesium sulphate
  11. customevaporated to dryness under reduced pressure
  12. customchromatographed
  13. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-4ba8ad696ece4e0e946d43b9dee0ad76
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487111B2

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