Hydrogen Peroxide → HCID 23369640, compound

HRID 1900730Notes

Reaction equation

HRID 1900730 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH:16]=[CH2:17])[O:13][C:5]2=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.C12BC(CCC1)CCC2.[OH-:27].[Na+].OO>O1CCCC1>[OH:27][CH2:17][CH2:16][CH:14]1[O:13][C:5]2=[C:6]3[C:11](=[C:2]([CH3:1])[CH:3]=[C:4]2[CH2:15]1)[NH:10][C:9](=[O:12])[CH:8]=[CH:7]3

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 23369618HCID 23369618, compound

Product 1

HCID 23369640HCID 23369640, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-2,3,6,7-tetrahydro-2-vinylfuro[2,3-f]quinoline-7-one (2.17 g) was suspended in tetrahydrofuran (40 ml). 9-Borabicyclo[3.3.1]nonan (0.5 mol, tetrahydrofuran solution, 80 ml) was added thereto while cooling on ice, and the mixture was stirred for 5.5 hours. Subsequently, aqueous 3N-NaOH solution (20 ml) and aqueous 35% hydrogen peroxide (20 ml) were added to the mixture in this order, and the temperature was raised to room temperature. After stirring for 30 minutes, extraction was performed with a solvent mixture of chloroform-methanol (4:1). The organic phase was dried and condensed under reduced pressure. The residue was recrystallized from a solvent mixture of chloroform-ethyl acetate-ether to obtain 1.7 g of 2-(2-hydroxyethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as pale yellow powdery crystals (72.6%).

Workup

  1. temperaturewhile cooling on ice
  2. stirringAfter stirring for 30 minutes
  3. extractionextraction
  4. additionwas performed with a solvent mixture of chloroform-methanol (4:1)
  5. customThe organic phase was dried
  6. customcondensed under reduced pressure
  7. customThe residue was recrystallized from a solvent mixture of chloroform-ethyl acetate-ether

Sources & evidence

ORD record
ord-f6865e9bb37a41aea1b34660bfe684ad
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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