HCID 23369675, compound → HCID 23369777, compound

HRID 1900736Notes

Reaction equation

HRID 1900736 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:15]([CH:16]=C)[CH2:14][O:13][C:5]2=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.I([O-])(=O)(=O)=[O:19].[Na+]>C(O)CCC.CC(C)=O.O.[Os](=O)(=O)(=O)=O>[CH:16]([CH:15]1[C:4]2[C:5](=[C:6]3[C:11](=[C:2]([CH3:1])[CH:3]=2)[NH:10][C:9](=[O:12])[CH:8]=[CH:7]3)[O:13][CH2:14]1)=[O:19]

Participants

5

Reactant 2

HCID 23369675HCID 23369675, compoundHCID 23667635Sodium periodate

Product 1

HCID 23369777HCID 23369777, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18506713HCID 18506713, compoundSolvent

Procedure

5-Methyl-2,3,6,7-tetrahydro-3-vinylfuro[2,3-f]quinoline-7-one (1.75 g) was dissolved in a mixture of butanol-acetone-water (3:3:1, 350 ml), to which sodium periodate (11.5 g) and osmium tetraoxide (350 mg) were added, followed by stirring at room temperature for 24 hours. The reaction mixture was filtered, and the filtrate was subjected to distillation to remove the solvent. The residue was recrystallized from a solvent mixture of chloroform-ether to obtain 1.05 g of 3-formyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as pale yellow needles (59.5%).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered
  3. distillationthe filtrate was subjected to distillation
  4. customto remove the solvent
  5. customThe residue was recrystallized from a solvent mixture of chloroform-ether

Sources & evidence

ORD record
ord-cba51d6f0d1c4a928a0347b5469ead4a
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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