2-Acetyl-5-hydroxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione → 2-Acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione

HRID 495079Notes

Reaction equation

HRID 495079 reaction equation
[C:1]([CH:4]1[O:8][C:7]2[C:9](=[O:19])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH2:5]1)=[C:14]([OH:18])[CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([C:4]1[O:8][C:7]2[C:9](=[O:19])[C:10]3[C:15]([C:16](=[O:17])[C:6]=2[CH:5]=1)=[C:14]([OH:18])[CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 177479482-Acetyl-5-hydroxy-2,3-dihydronaphtho[2,3-b]furan-4,9-dione

Product 1

HCID 100152592-Acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dioneYield 52%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

To a solution of 2-acetyl-2,3-dihydro-5-hydroxynaphtho[2,3-b]furan-4,9-dione (IX) (0.5 g, 1.95 mmol) in chloroform (50 mL) is added manganese dioxide manufactured by Aldrich (90% activated manganese dioxide, 10 micron, 10 g), and the resulting suspension is heated to reflux for 1 day. The suspension is cooled to room temperature, and then the mixture is filtered. The filtrate is evaporated in vacuo, and the residue is purified by silica gel column chromatography (eluent:chloroform) to give 2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione (I) 0.26 g (51%).

Workup

  1. temperaturethe resulting suspension is heated
  2. temperatureto reflux for 1 day
  3. filtrationthe mixture is filtered
  4. customThe filtrate is evaporated in vacuo
  5. customthe residue is purified by silica gel column chromatography (eluent:chloroform)

Sources & evidence

ORD record
ord-54c73e05b61c44d28cf361b41d99ce9a
Source dataset
uspto-grants-2009_05
Patent number
US07538234B2

Reaction notes

Loading…