Hydrogen Bromide → 2-(4-Hydroxyphenyl)-pyrano[3,2-b]pyridin-4-one

HRID 884697노트

반응식

HRID 884697 반응식
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:21])[CH2:10][C:11]([C:13]2[C:18](OC)=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:5][CH:4]=1.Br.C([O-])(O)=O.[Na+]>CCOC(C)=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:21][C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[C:11](=[O:12])[CH:10]=2)=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 57555827HCID 57555827, 화합물

생성물 1

HCID 116372872-(4-Hydroxyphenyl)-pyrano[3,2-b]pyridin-4-one수율 3.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

In 50 mL round-bottom flask fitted with magnetic stirrer were placed 1-(4-methoxyphenyl)-3-(3-methoxypyridin-2-yl) propane-1,3-dione (4.68 g, 16 mmol) and 45% aqueous solution of HBr (25 mL). The reaction mixture was refluxed for 3 h, then cooled down to rt. Solid NaHCO3 was used to adjust pH to 7, followed by EtOAc (30 mL). The organic layer was separated and aqueous layer was extracted with EtOAc (2×30 mL). The combined organic extracts were dried over Na2SO4, concentrated to give the crude product, which was purified by column chromatography using 30% MeOH in EtOAc to give 125 mg of 2-(4-hydroxy-phenyl)-pyrano[3,2-b]pyridin-4-one (3.2%). MS (ES) m/z: 240.09 (M+1), and 149.06.

후처리

  1. customIn 50 mL round-bottom flask fitted with magnetic stirrer
  2. temperatureThe reaction mixture was refluxed for 3 h
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with EtOAc (2×30 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-b2badddda967447087f34bf3b908d1a2
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242130B2

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