1h-furo[3,4-b]chromene-3,9-dione → HCID 86742410, compound

HRID 622076Notes

Reaction equation

HRID 622076 reaction equation
[CH2:1]1[C:9]2[C:8](=O)[C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[O:5][C:4]=2[C:3](=[O:15])[O:2]1.[H][H]>C(O)(=O)C.[Pd].C(OCC)(=O)C>[CH2:1]1[C@H:9]2[C@H:4]([O:5][C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[CH2:8]2)[C:3](=[O:15])[O:2]1

Participants

6

Reactant 2

HCID 2247871h-furo[3,4-b]chromene-3,9-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 86742410HCID 86742410, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1H-furo[3,4-b][1]benzopyran-3,9-dione (6.1 g) in glacial acetic acid (300 ml) was hydrogenated over 10% palladium on charcoal (1 g) until hydrogen uptake ceased. The catalyst was filtered off and the solvent evaporated from the filtrate to give an oil. The oil was dissolved in ethyl acetate and the solution washed with aqueous sodium bicarbonate and brine. The organic layer was separated, dried (MgSO4) and the solvent evaporated. Crystallisation of the residue from ethyl acetate/ether gave the title compound (3.85 g) m.p. 107°-111°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated from the filtrate
  3. customto give an oil
  4. washthe solution washed with aqueous sodium bicarbonate and brine
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent evaporated
  8. customCrystallisation of the residue from ethyl acetate/ether

Sources & evidence

ORD record
ord-410eef924f7d4f479b619eb5439fd681
Source dataset
uspto-grants-1988_09
Patent number
US04769367

Reaction notes

Loading…