HCID 18519051, compound → HCID 18519023, compound

HRID 1369280Notes

Reaction equation

HRID 1369280 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:24](=[CH:25][CH:26]=1)[C:17]1[CH:18]([O:22][CH3:23])[O:19][C:20](=[O:21])[C:16]=1[CH:15]=[CH:14]2)=[O:10])C1C=CC=CC=1>CCO.C1COCC1.[Pd]>[OH:10][C:9]([C:11]1[CH:12]=[C:13]2[C:24](=[CH:25][CH:26]=1)[C:17]1[CH:18]([O:22][CH3:23])[O:19][C:20](=[O:21])[C:16]=1[CH:15]=[CH:14]2)=[O:8]

Participants

5

Reactant 1

HCID 18519051HCID 18519051, compound

Product 1

HCID 18519023HCID 18519023, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-benzyloxycarbonyl-1-methoxynaphtho[1,2-c]furan-3(1H)-one (33 mg, 0.095 mmol) and a catalytic amount of 10% Pd/C in 2 mL of EtOH was stirred at rt under an atmosphere of H2 (balloon) for 2 h. The mixture was then diluted with THF and filtered through a pad of Celite. The filtrate was then concentrated in vacuo. The crude material was dissolved in saturated aqueous NaHCO3 and washed with EtOAc. The aqueous layer was then acidified with 1 M aqueous HCl and extracted with EtOAc. The extract was dried over MgSO4 and concentrated in vacuo affording 19 mg (79%).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was then concentrated in vacuo
  3. dissolutionThe crude material was dissolved in saturated aqueous NaHCO3
  4. washwashed with EtOAc
  5. extractionextracted with EtOAc
  6. dry with materialThe extract was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customaffording 19 mg (79%)

Sources & evidence

ORD record
ord-2b6e8c577686437c90af73a4d19c4c47
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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