HCID 12085334, compound → HCID 12085335, compound

HRID 896444Notes

Reaction equation

HRID 896444 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH:14]=[C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:16]2)=[CH:11][C:10]=1[O:25][CH3:26])C1C=CC=CC=1>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:16]2)=[CH:11][C:10]=1[O:25][CH3:26]

Participants

5

Reactant 1

HCID 12085334HCID 12085334, compound

Product 1

HCID 12085335HCID 12085335, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7.5 mmol of ethyl 7-(benzyloxy)-6-methoxy-4-oxo-4H-chromen-2-carboxylate in 60 ml of ethyl acetate and 30 ml of glacial acetic acid is hydrogenated in the presence of 1.2 g of 10% palladium on carbon at 3 bar and 50° C. After 4 days, the hydrogenation is terminated and the mixture is diluted with ethyl acetate. The mixture is filtered through kieselguhr and the filtrate is concentrated under reduced pressure. The residue is taken up in ethyl acetate and the organic phase is washed with water and saturated sodium chloride solution. The mixture is dried over sodium sullfate and concentrated, giving ethyl 7-hydroxy-6-methoxy-2-chromancarboxylate in a yield of 94% as a colorless oil which is directly reacted further.

Workup

  1. customthe hydrogenation is terminated
  2. additionthe mixture is diluted with ethyl acetate
  3. filtrationThe mixture is filtered through kieselguhr
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. washthe organic phase is washed with water and saturated sodium chloride solution
  6. dry with materialThe mixture is dried over sodium sullfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3c33137017a7421c95b9775b61f6a747
Source dataset
uspto-grants-2005_07
Patent number
US06919360B2

Reaction notes

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